Reaxys
PubChem
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Reactions (229)
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Substances (107)
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References
100
Synthesize Find similar With sodium tetrahydroborate in ethanol
T=20°C; 0.5 h;
101
Synthesize Find similar
Rx-ID: 37779930 Find similar reactions
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
Synthesize Find similar
Rx-ID: 37779860 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 20 °C 2: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C View Scheme
Synthesize Find similar
Synthesize Find similar
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
102
Synthesize Find similar With sodium tetrahydroborate in ethanol
T=20°C; 0.5 h;
Synthesize Find similar
Rx-ID: 37779940 Find similar reactions
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
103
Synthesize Find similar With sodium tetrahydroborate in ethanol
T=20°C; 0.5 h;
Synthesize Find similar
Rx-ID: 37779824 Find similar reactions
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
104
Rx-ID: 37779915
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Synthesize Find similar
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Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 20 °C 2: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C View Scheme
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
105
Synthesize Find similar With sodium tetrahydroborate in ethanol
T=20°C; 0.5 h;
Synthesize Find similar
Rx-ID: 37779825 Find similar reactions
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
106
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Rx-ID: 37779917 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 20 °C 2: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C View Scheme
Synthesize Find similar
Synthesize Find similar
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
107
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Synthesize Find similar
Rx-ID: 4005348 Find similar reactions
With borane in tetrahydrofuran
18 h; Heating;
Glennon; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis
Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 1929 - 1935 Title/Abstract Full Text View citing articles Show Details
108
Synthesize Find similar Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 4h 2: BH3 / tetrahydrofuran / 18 h / Heating View Scheme
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Rx-ID: 18233587 Find similar reactions
Glennon; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis
Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 1929 - 1935 Title/Abstract Full Text View citing articles Show Details
109
Synthesize Find similar Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 4h 2: BH3 / tetrahydrofuran / 18 h / Heating View Scheme
Synthesize Find similar
Rx-ID: 18234312 Find similar reactions
Glennon; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis
Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 1929 - 1935 Title/Abstract Full Text View citing articles Show Details
110
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Rx-ID: 37779837 Find similar reactions
Multi-step reaction with 2 steps
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Synthesize Find similar
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael;
1: triethylamine / ethanol / 20 °C 2: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C View Scheme
Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
111
Synthesize Find similar With sodium tetrahydroborate in ethanol
T=20°C; 0.5 h;
Synthesize Find similar
Rx-ID: 37779928 Find similar reactions
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
112
Synthesize Find similar
Rx-ID: 43732276 Find similar reactions
23%
Stage #1: With triethylamine in ethanol
Stage #2: With sodium tetrahydroborate in ethanol
0.5 h; Stage #3: With hydrogenchloride in diethyl ether; ethyl acetate
Synthesize Find similar
Synthesize Find similar
Petersen, Ida Nymann; Villadsen, Jonas; Hansen, Hanne Demant; Jensen, Anders A.; Lehel, Szabolcs; Gillings, Nic; Herth, Matthias M.; Knudsen, Gitte M.; Kristensen, Jesper L.
Bioorganic and Medicinal Chemistry, 2016 , vol. 24, # 21 p. 5353 - 5356 Title/Abstract Full Text Show Details
Hide Experimental Procedure
General procedure A reductive animation
General procedure: The amine (1 eq and aldehyde (1,1 eq) was dissolved in EtOH (0.5 mmol/ml) and added a drop of Et3N. When TLC indicated full conversion to the imine (1-48 h), NaBH4 (2 eq) was added and the mixture was further stirred for 30 min. The volume was reduced and the mixture was added water and extracted with DCM, evaporated on celite and purified in flash column chromatography (5 percent Et3N in EtOAc), redissolved in EtOAc participated as the HCl salt using 2 M HCl in diethyl ether (Sigma Aldrich).
113
Synthesize Find similar
Rx-ID: 37779866 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 20 °C 2: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C View Scheme
Synthesize Find similar
Synthesize Find similar
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
114
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With sodium tetrahydroborate in ethanol
T=20°C; 0.5 h;
Synthesize Find similar
Rx-ID: 37779943 Find similar reactions
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
115
Synthesize Find similar
Rx-ID: 43732278 Find similar reactions
66%
Stage #1: With triethylamine in ethanol
Stage #2: With sodium tetrahydroborate in ethanol
0.5 h; Hide Experimental Procedure
Synthesize Find similar
Synthesize Find similar
Petersen, Ida Nymann; Villadsen, Jonas; Hansen, Hanne Demant; Jensen, Anders A.; Lehel, Szabolcs; Gillings, Nic; Herth, Matthias M.; Knudsen, Gitte M.; Kristensen, Jesper L.
Bioorganic and Medicinal Chemistry, 2016 , vol. 24, # 21 p. 5353 - 5356 Title/Abstract Full Text Show Details
General procedure A reductive animation
General procedure: The amine (1 eq and aldehyde (1,1 eq) was dissolved in EtOH (0.5 mmol/ml) and added a drop of Et3N. When TLC indicated full conversion to the imine (1-48 h), NaBH4 (2 eq) was added and the mixture was further stirred for 30 min. The volume was reduced and the mixture was added water and extracted with DCM, evaporated on celite and purified in flash column chromatography (5 percent Et3N in EtOAc), redissolved in EtOAc participated as the HCl salt using 2 M HCl in diethyl ether (Sigma Aldrich).
116
Synthesize Find similar With borane in tetrahydrofuran
18 h; Heating;
Synthesize Find similar
Rx-ID: 4004888 Find similar reactions
Glennon; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis
Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 1929 - 1935 Title/Abstract Full Text View citing articles Show Details
117
Synthesize Find similar Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 4h 2: BH3 / tetrahydrofuran / 18 h / Heating View Scheme
Synthesize Find similar
Rx-ID: 18233455 Find similar reactions
Glennon; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis
Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 1929 - 1935 Title/Abstract Full Text View citing articles Show Details
118
Synthesize Find similar Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 4h 2: BH3 / tetrahydrofuran / 18 h / Heating
Synthesize Find similar
Rx-ID: 18234309 Find similar reactions
Glennon; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis
Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 1929 - 1935 Title/Abstract Full Text View citing articles Show Details
View Scheme
119
Synthesize Find similar With sodium tetrahydroborate in ethanol
T=20°C; 0.5 h;
Synthesize Find similar
Rx-ID: 37779828 Find similar reactions
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
120
Synthesize Find similar
Rx-ID: 37779923 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 20 °C 2: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C View Scheme
Synthesize Find similar
Synthesize Find similar
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
121
Synthesize Find similar
Rx-ID: 43732274 Find similar reactions
56%
Stage #1: With triethylamine in ethanol
Stage #2: With sodium tetrahydroborate in ethanol
Synthesize Find similar
Synthesize Find similar
Petersen, Ida Nymann; Villadsen, Jonas; Hansen, Hanne Demant; Jensen, Anders A.; Lehel, Szabolcs; Gillings, Nic; Herth, Matthias M.; Knudsen, Gitte M.; Kristensen, Jesper L.
Bioorganic and Medicinal Chemistry, 2016 , vol. 24, # 21 p. 5353 - 5356 Title/Abstract Full Text Show Details
0.5 h; Stage #3: With hydrogenchloride in diethyl ether; ethyl acetate
Hide Experimental Procedure
General procedure A reductive animation
General procedure: The amine (1 eq and aldehyde (1,1 eq) was dissolved in EtOH (0.5 mmol/ml) and added a drop of Et3N. When TLC indicated full conversion to the imine (1-48 h), NaBH4 (2 eq) was added and the mixture was further stirred for 30 min. The volume was reduced and the mixture was added water and extracted with DCM, evaporated on celite and purified in flash column chromatography (5 percent Et3N in EtOAc), redissolved in EtOAc participated as the HCl salt using 2 M HCl in diethyl ether (Sigma Aldrich).
122
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Schiff'sche Base 4b, NaBH4;
Rx-ID: 7857103 Find similar reactions
Josio et al.
Heterocycles, 1978 , vol. 9, p. 1,3 Full Text Show Details
123
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Schiff'sche Base 4a, NaBH4;
Rx-ID: 7859006 Find similar reactions
Josio et al.
Heterocycles, 1978 , vol. 9, p. 1,3 Full Text Show Details
124
Rx-ID: 37779844
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Synthesize Find similar
Synthesize Find similar
Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 20 °C 2: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C View Scheme
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
125
Synthesize Find similar With sodium tetrahydroborate in ethanol
T=20°C; 0.5 h;
Synthesize Find similar
Rx-ID: 37779931 Find similar reactions
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
126
Synthesize Find similar With borane in tetrahydrofuran
18 h; Heating;
Synthesize Find similar
Rx-ID: 4006975 Find similar reactions
Glennon; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis
Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 1929 - 1935 Title/Abstract Full Text View citing articles Show Details
127
Synthesize Find similar Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 4h
Synthesize Find similar
Rx-ID: 18233729 Find similar reactions
Glennon; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis
Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 1929 - 1935 Title/Abstract Full Text View citing articles Show Details
2: BH3 / tetrahydrofuran / 18 h / Heating View Scheme
128
Synthesize Find similar Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 4h 2: BH3 / tetrahydrofuran / 18 h / Heating View Scheme
Synthesize Find similar
Rx-ID: 18234313 Find similar reactions
Glennon; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis
Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 1929 - 1935 Title/Abstract Full Text View citing articles Show Details
129
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Synthesize Find similar
Rx-ID: 29384962 Find similar reactions
With sodium tetrahydroborate in methanol
5 h; Reflux;
Wang, Yan-Xiang; Wang, Yu-Ping; Zhang, Hao; Kong, Wei-Jia; Li, Ying-Hong; Liu, Fei; Gao, Rong-Mei; Liu, Ting; Jiang, Jian-Dong; Song, Dan-Qing
Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 21 p. 6004 - 6008 Title/Abstract Full Text View citing articles Show Details
Stage #1: With sodium tetrahydroborate in methanol
T=20°C; 5 h; Reflux; Stage #2: With hydrogenchloride in water
pH=5 - 6; Hide Experimental Procedure
Wang, Yan-Xiang; Kong, Wei-Jia; Li, Ying-Hong; Tang, Sheng; Li, Zheng; Li, Yang-Biao; Shan, YongQiang; Bi, Chong-Wen; Jiang, Jian-Dong; Song, Dan-Qing
Bioorganic and Medicinal Chemistry, 2012 , vol. 20, # 22 p. 6552 - 6558 Title/Abstract Full Text View citing articles Show Details
General procedure to obtain final dibenzo-quinolizine analogues
General procedure: The requisite substituted phenylethylamine and benzaldehyde were purchased commercially. A 250 mL round bottom flask was charged with the corresponding substituted phenylethylamine (1, 1.0 equiv) and substituted benzaldehyde (2, 1.0 equiv) at 70 °C, and the mixture was stirred under vacuum for 1 h. Then, 100 mL methanol was added to solve the residue. To this solution, NaBH4 (3.0 equiv) was added portionwise at the room temperature. The mixture was stirred under gentle reflux for 4 h. Upon completion, as determined by TLC, the reaction mixture was concentrated in vacuo. The residue was dissolved in water (300 mL). The resulting aqueous phase was extracted with ethyl acetate (3 × 100 mL) and the combined organic layers were rinsed with saturated brines (100 mL), dried (Na2SO4). Concentrated hydrochloric acid was added dropwise to adjust pH of the organic layer to 5-6, and filter to give the hydrochlorate (4) without further purification. To a suspension of anhydrous CuSO4 (3.6 equiv) and corresponding hydrochlorate (4, 1.0 equiv) in anhydrous formic acid (45 mL) was added 40percent glyoxal solution (2.0 equiv) at 100 °C. The reaction mixture was stirred at 100 °C for 5 h, concentrated hydrochloric acid (0.8 and 0.6 equiv) was added respectively at 2 h and 4 h through this process. Upon completion, as determined by TLC, the mixture was filtered. The filtrate was concentrated in vacuo. The residue was dissolved in methanol (500 mL) and water (10 mL), CaO was added portionwise to adjust pH to 9-10. The suspension was stirred at the room temperature for 2 h, filtered and concentrated in vacuo. The resulting residue was purified via flash column chromatography using methanol/dichloromethane as the eluent to give 6.
130
Synthesize Find similar With sodium tetrahydroborate in methanol
5 h; Reflux;
Synthesize Find similar
Rx-ID: 29384964 Find similar reactions
Wang, Yan-Xiang; Wang, Yu-Ping; Zhang, Hao; Kong, Wei-Jia; Li, Ying-Hong; Liu, Fei; Gao, Rong-Mei; Liu, Ting; Jiang, Jian-Dong; Song, Dan-Qing
Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 21 p. 6004 - 6008 Title/Abstract Full Text View citing articles Show Details
131
Synthesize Find similar Multi-step reaction with 2 steps 1.1: neat (no solvent) / 1 h / 70 °C 2.1: sodium tetrahydroborate / methanol / 5 h / 20 °C / |Reflux 2.2: pH 5 - 6 View Scheme
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Rx-ID: 34393804 Find similar reactions
Wang, Yan-Xiang; Kong, Wei-Jia; Li, Ying-Hong; Tang, Sheng; Li, Zheng; Li, Yang-Biao; Shan, YongQiang; Bi, Chong-Wen; Jiang, Jian-Dong; Song, Dan-Qing
Bioorganic and Medicinal Chemistry, 2012 , vol. 20, # 22 p. 6552 - 6558 Title/Abstract Full Text View citing articles Show Details
132
Synthesize Find similar Multi-step reaction with 2 steps 1.1: neat (no solvent) / 1 h / 70 °C 2.1: sodium tetrahydroborate / methanol / 5 h / 20 °C / |Reflux 2.2: pH 5 - 6 View Scheme
Synthesize Find similar
Rx-ID: 34393844 Find similar reactions
Wang, Yan-Xiang; Kong, Wei-Jia; Li, Ying-Hong; Tang, Sheng; Li, Zheng; Li, Yang-Biao; Shan, YongQiang; Bi, Chong-Wen; Jiang, Jian-Dong; Song, Dan-Qing
Bioorganic and Medicinal Chemistry, 2012 , vol. 20, # 22 p. 6552 - 6558 Title/Abstract Full Text View citing articles Show Details
133
Synthesize Find similar
Rx-ID: 43732275 Find similar reactions
64%
Stage #1: With triethylamine in ethanol
Stage #2: With sodium tetrahydroborate in ethanol
0.5 h; Stage #3: With hydrogenchloride in diethyl ether; ethyl acetate
Synthesize Find similar
Synthesize Find similar
Petersen, Ida Nymann; Villadsen, Jonas; Hansen, Hanne Demant; Jensen, Anders A.; Lehel, Szabolcs; Gillings, Nic; Herth, Matthias M.; Knudsen, Gitte M.; Kristensen, Jesper L.
Bioorganic and Medicinal Chemistry, 2016 , vol. 24, # 21 p. 5353 - 5356 Title/Abstract Full Text Show Details
Hide Experimental Procedure
General procedure A reductive animation
General procedure: The amine (1 eq and aldehyde (1,1 eq) was dissolved in EtOH (0.5 mmol/ml) and added a drop of Et3N. When TLC indicated full conversion to the imine (1-48 h), NaBH4 (2 eq) was added and the mixture was further stirred for 30 min. The volume was reduced and the mixture was added water and extracted with DCM, evaporated on celite and purified in flash column chromatography (5 percent Et3N in EtOAc), redissolved in EtOAc participated as the HCl salt using 2 M HCl in diethyl ether (Sigma Aldrich).
134
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Stage #1: With sodium tetrahydroborate; ethanol
0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
Hide Experimental Procedure
Synthesize Find similar
Rx-ID: 40160330 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
4.1. General procedure for the synthesis of N-benzylatedphenethylamines 1b–u
General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products. 3-((4-bromo-2,5-dimethoxyphenethylamino)methyl)phenol hydrochloride (1u); Obtained from 2C-B·HCl and 3-methoxybenzaldehyde by general procedure A in 68percent yield as an off-white solid. mp. 223 °C. 1H NMR (400 MHz, DMSO-d6) δ 9.70 (s, 1H), 9.35 (s, 2H), 7.25 – 7.17 (m, 2H), 7.19 (s, 1H), 7.01 (s, 1H), 6.95 (d, J = 12.7 Hz, 2H), 6.82 (dd, J = 8.1, 2.1 Hz,
1H), 4.05 (t, J = 5.0 Hz, 2H), 3.79 (s, 3H), 3.75 (s, 3H), 3.11 – 2.91 (m, 4H). 13C NMR (100 MHz, DMSO-d6) δ 157.5, 151.5, 149.4, 133.1, 129.6, 125.5, 120.4, 116.9, 115.9, 115.8, 115.0, 108.9, 56.6, 56.2, 49.8, 45.6, 26.4.
135
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Rx-ID: 40160355 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol 2: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
Synthesize Find similar
Synthesize Find similar
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
136
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Multi-step reaction with 3 steps 1: hydrochlorid acid; hydrogen peroxide / water / 2 h / 100 °C / |Sealed tube 2: triethylamine / ethanol 3: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
Synthesize Find similar
Rx-ID: 40160304 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
137
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Multi-step reaction with 2 steps 1: triethylamine / ethanol 2: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
Synthesize Find similar
Rx-ID: 40160308 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
138
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Stage #1: With sodium tetrahydroborate; ethanol
0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
Hide Experimental Procedure
Synthesize Find similar
Rx-ID: 40160319 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
4.1. General procedure for the synthesis of N-benzylatedphenethylamines 1b–u
General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products. 3-((4-bromo-2,5-dimethoxyphenethylamino)methyl)pyridin-2(1H)-one hydrochloride (1i); Obtained from 2C-B·HCl and 7 by general procedure A in 62percent yield as an off-white solid. mp. 186 – 188 °C. 1H NMR (300 Mhz, DMSO-d6) δ 12.09 (br s, 1H), 9.20 (br s, 2H), 7.72 (dd, J = 6.7, 1.8 Hz, 1H), 7.47 (dd, J = 6.4, 1.8 Hz, 1H), 7.17 (s, 1H), 7.02 (s, 1H), 6.27 (dd, J
= 6.7, 6.4 Hz, 1H), 3.96 (s, 2H), 3.79 (s, 3H), 3.75 (s, 3H), 3.11 – 2.91 (m, 4H). 13C NMR (75 MHz, DMSO-d6) δ 161.8, 151.3, 149.2, 142.2, 136.2, 125.3, 121.9, 115.7, 114.9, 108.7, 104.9, 56.6, 56.2, 45.8, 45.5, 26.3
139
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140
Multi-step reaction with 4 steps 1.1: 2,2,6,6-tetramethylpiperidinyl-lithium / tetrahydrofuran / 2.58 h / -78 °C 1.2: 0.5 h / -78 - -40 °C 2.1: hydrochlorid acid; hydrogen peroxide / water / 2 h / 100 °C / |Sealed tube 3.1: triethylamine / ethanol 4.1: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160364 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
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Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide / 18 h / 20 °C 2: trifluoroacetic acid / N,N-dimethyl-formamide; dichloromethane / 0.25 h View Scheme
Rx-ID: 40783690 Find similar reactions
Prabhakaran, Jaya; Underwood, Mark D.; Kumar, J.S. Dileep; Simpson, Norman R.; Kassir, Suham A.; Bakalian, Mihran J.; Mann, J. John; Arango, Victoria
Bioorganic and Medicinal Chemistry Letters, 2015 , vol. 25, # 18 art. no. 22923, p. 3933 - 3936 Title/Abstract Full Text View citing articles Show Details
141
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98 mg
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With trifluoroacetic acid in dichloromethane; N,Ndimethyl-formamide
0.25 h; Hide Experimental Procedure
Rx-ID: 40783693 Find similar reactions
Prabhakaran, Jaya; Underwood, Mark D.; Kumar, J.S. Dileep; Simpson, Norman R.; Kassir, Suham A.; Bakalian, Mihran J.; Mann, J. John; Arango, Victoria
Bioorganic and Medicinal Chemistry Letters, 2015 , vol. 25, # 18 art. no. 22923, p. 3933 - 3936 Title/Abstract Full Text View citing articles Show Details
tert-Butyl 4-bromo-2,5-dimethoxyphenethyl(2-(2-fluoroethoxy) benzyl)carbamate (nonradioactive standard
In a two necked RB flask containing sodium hydride (30.72mg, 4mmol (60percent emulsion)), a solution of tert-butyl 4-bromo-2,5-dimethoxy-phenethyl(2-hydroxybenzyl) carbamate (2, 150mg, 0.32mmol) dissolved in 1mL of anhydrous DMF was added slowly. The mixture was stirred at room temperature for 15min followed by the addition of 1-bromo-2-fluoroethane (51mg, 0.4mmol) and the contents were stirred for 18h. After completion of the reaction, as indicated by TLC (25percent ethyl acetate in hexane), a 1:1 mixture of trifluoroacetic acid and dichloromethane (1mL) was added to the above solution and the contents were stirred for an additional 15min. When the reaction was completed according to TLC, the solution was diluted with ethyl acetate (25mL) and washed with saturated aqueous sodium bicarbonate, followed by water and brine. The combined organic phase was extracted and dried over anhydrous magnesium sulfate. Evaporation of ethyl acetate in a rotary evaporator under vacuum provided the crude product, which was then purified by silica gel column chromatography using 20percent ethyl acetate in hexane. The product fraction was isolated and the combined fractions were evaporated and dried under high vacuum to obtain the final product in 75percent yield (98mg). 1H NMR (300MHz, CDCl3): 7.3 (m, 2H), 6.9 (m, 4H), 4.7 (d, J=8.5, 2H), 4.2 (dm, 2H), 3.9–3.7 (m, 8H), 2.9 (m, 4H); HRMS calculated for C19H23BrFNO3, 411.0845; found, 412.0924
(MH+).
142
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Rx-ID: 23301898
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S*BIO PTE LTD
Patent: WO2005/40161 A1, 2005 ; Location in patent: Page/Page column 86-87; 89 ;
Title/Abstract Full Text Show Details
143
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Rx-ID: 37779831 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 20 °C 2: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C View Scheme
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Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
144
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With sodium tetrahydroborate in ethanol
T=20°C; 0.5 h;
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Rx-ID: 37779925 Find similar reactions
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
145
Rx-ID: 37779833
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Multi-step reaction with 2 steps 1: triethylamine / ethanol / 20 °C 2: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C View Scheme
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
146
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With sodium tetrahydroborate in ethanol
T=20°C; 0.5 h;
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Rx-ID: 37779926 Find similar reactions
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
147
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Stage #1: With sodium tetrahydroborate; ethanol
0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
Hide Experimental Procedure
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Rx-ID: 40160329 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
4.1. General procedure for the synthesis of N-benzylatedphenethylamines 1b–u
General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products. 2-(4-bromo-2,5-dimethoxyphenyl)-N-(3-methoxybenzyl)ethanamine hydrochloride (1t); Obtained from 2C-B·HCl and 3-methoxybenzaldehyde by general procedure A in 79percent yield as a colorless solid. mp. 157 °C. 1H NMR (400 MHz, DMSO-d6) δ 9.48 (s, 2H), 7.34 (t, J = 7.9 Hz, 1H), 7.24 (d, J = 2.1, 0.8 Hz, 1H), 7.19 (s, 1H), 7.11 (d, J = 7.5 Hz, 1H), 7.02 (s, 1H),
6.97 (dd, J = 8.2, 2.1 Hz, 1H), 4.12 (t, J = 5.3 Hz, 2H), 3.79 (s, 3H), 3.78 (s, 3H), 3.74 (s, 3H), 3.10 – 2.94 (m, 4H). 13C NMR (100 MHz, DMSO-d6) δ 159.3, 151.5, 149.4, 133.4, 129.7, 125.5, 122.0, 115.9, 115.5, 115.0, 114.4, 108.9, 56.6, 56.2, 55.2, 49.7, 45.5, 26.4.
148
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Rx-ID: 40160353 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol 2: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
149
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Rx-ID: 7777920 Find similar reactions
Mescalin, entspr. Aldehyd, H2;
Hexachimie
Patent: FR2328457 , 1977 ; Chem.Abstr., vol. 88, # 74105 Full Text Show Details
150
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Stage #1: With sodium tetrahydroborate; ethanol
0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
Hide Experimental Procedure
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Rx-ID: 40160321 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
4.1. General procedure for the synthesis of N-benzylatedphenethylamines 1b–u
General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products. 2-(4-bromo-2,5-dimethoxyphenyl)-N-(pyridin-2-ylmethyl)ethanamine dihydrochloride (1k); Obtained from 2C-B·HCl and picolinaldehyde by general procedure A in 76percent yield as a colorless solid. mp. 187 – 189 °C. 1H NMR (300 Mhz, DMSO-d6) δ 10.02 (br s, 1H), 9.97 (br s, 2H), 8.73 (ddd, J = 5.1, 1.7, 0.8 Hz, 1H), 8.15 (ddd, J = 7.8, 7.6, 1.7 Hz, 1H), 7.91 (ddd, J =
7.9, 1.2, 0.8 Hz, 1H), 7.64 (ddd, J = 7.6, 5.1, 1.2 Hz, 1H), 7.17 (s, 1H), 7.03 (s, J = 4.7 Hz, 1H), 4.44 (s, 2H), 3.78 (s, 3H), 3.74 (s, 3H), 3.25 – 3.11 (m, 2H), 3.07 – 2.97 (m, 2H). 13C NMR (75 MHz, DMSO-d6) δ 151.3, 150.0, 149.2, 146.4, 140.3, 125.3, 125.2, 124.8, 115.7, 114.9, 108.8, 56.7, 56.3, 48.7, 46.2, 26.4
151
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Stage #1: With sodium tetrahydroborate; ethanol
0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
Hide Experimental Procedure
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Rx-ID: 40160322 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
4.1. General procedure for the synthesis of N-benzylatedphenethylamines 1b–u
General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products. 2-(4-bromo-2,5-dimethoxyphenyl)-N-(pyridin-3-ylmethyl)ethanamine dihydrochloride (1l); Obtained from 2C-B·HCl and nicotinaldehyde by general procedure A in 81percent yield as an off-white solid. mp. 207 – 210 °C. 1H NMR (300 Mhz, DMSO-d6) δ 10.22 (br s, 1H), 10.17 (br s, 2H), 9.13 (dd, J = 1.9, 1.5 Hz, 1H), 8.91 (dd, J = 5.6, 1.5 Hz, 1H), 8.79 (ddd, J = 8.1, 1.9,
0.5 Hz, 1H), 8.05 (ddd, J = 8.1, 5.6, 0.5 Hz, 1H), 7.17 (s, 1H), 7.04 (s, 1H), 4.41 (s, 2H), 3.78 (s, 3H), 3.75 (s, J = 2.0 Hz, 3H), 3.20 – 3.08 (m, 2H), 3.06 – 2.96 (m, 2H). 13C NMR (75 MHz, DMSO-d6) δ 151.3, 149.2, 146.5, 144.0, 142.5, 131.4, 126.3, 125.2, 115.7, 114.9, 108.8, 56.7, 56.3, 46.3, 45.9, 26.4
152
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Stage #1: With sodium tetrahydroborate; ethanol
0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
Hide Experimental Procedure
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Rx-ID: 40160323 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
4.1. General procedure for the synthesis of N-benzylatedphenethylamines 1b–u
General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in
EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products. 2-(4-bromo-2,5-dimethoxyphenyl)-N-(pyridin-3-ylmethyl)ethanamine dihydrochloride (1m); Obtained from 2C-B·HCl and isonicotinaldehyde by general procedure A in 73percent yield as an off-white solid. mp. 227 °C dec. 1H NMR (300 Mhz, DMSO-d6) δ 10.38 (br s, 2H), 8.96 (d, J = 6.6 Hz, 2H), 8.26 (d, J = 6.6 Hz, 2H), 7.17 (s, 1H), 7.04 (s, 1H), 4.49 (s, 2H), 3.78 (s, 3H), 3.75 (s, 3H), 3.21 – 2.98 (m, 4H). 13C NMR (75 MHz, DMSO-d6) δ 151.3, 150.6, 149.2, 142.4 (2C), 127.1 (2C), 125.2, 115.7, 114.9, 108.8, 56.6, 56.35, 48.3, 46.2, 26.3
153
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Rx-ID: 40160336 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol 2: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
154
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Rx-ID: 40160338 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol 2: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
155
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Find similar Rx-ID: 40160340 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol 2: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Find similar
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
156
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Stage #1: With sodium tetrahydroborate; ethanol
0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
Hide Experimental Procedure
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Rx-ID: 40160318 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
4.1. General procedure for the synthesis of N-benzylatedphenethylamines 1b–u
General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products. N-((1H-indol-7-yl)methyl)-2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (1h); Obtained from 2C-B·HCl and 1H-indole-7-carbaldehyde by general procedure A in 59percent yield as a light pink solid. mp. 228 – 229 °C. 1H NMR (300 Mhz, DMSO-d6) δ 11.81 (s, 1H), 9.45 (br s, 2H), 7.59 (d, J = 7.8 Hz, 1H), 7.43 (dd, J = 3.0, 2.5 Hz, 1H), 7.32 (dd, J =
7.3, 0.9 Hz, 1H), 7.16 (s, 1H), 7.03 (dd, J = 7.8, 7.3 Hz, 1H), 7.00 (s, 1H), 6.50 (dd, J = 3.0, 1.7 Hz, 1H), 4.50 (s, 2H), 3.78 (s, 3H), 3.71 (s, 3H), 3.25 – 3.11 (m, 2H), 3.05 – 2.93 (m, 2H). 13C NMR (75 MHz, DMSO) δ 151.3, 149.2, 134.8, 128.1, 125.6, 125.4, 123.5, 121.0, 118.7, 115.7, 114.8, 108.7, 101.6, 56.6, 56.2, 46.4, 45.8, 26.5
157
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Rx-ID: 40160334 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol 2: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
158
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Stage #1: With sodium tetrahydroborate; ethanol
0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
Hide Experimental Procedure
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Rx-ID: 40160312 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
4.1. General procedure for the synthesis of N-benzylatedphenethylamines 1b–u
General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products. N-(benzofuran-7-ylmethyl)-2-(4-bromo-2,5-dimethoxyphenyl)ethanaminehydrochloride (1b); Obtained from 2C-B·HCl and 2 by general procedure A in 77percent yield as a colorless solid. mp. 200 – 202 °C. 1H NMR (300 Mhz, DMSO-d6) δ 9.80 (br s,2H), 8.09 (d, J = 2.2 Hz, 1H), 7.70 (dd, J = 7.7, 1.0 Hz, 1H), 7.65 (dd, J = 7.5, 1.0 Hz, 1H), 7.30 (dd, J = 7.7, 7.5 Hz, 1H),
7.17 (s, 1H), 7.03 (d, J = 2.5 Hz, 1H), 7.01 (s, 1H), 4.44 (s, 2H), 3.78 (s, 3H), 3.72 (s, 3H), 3.21 – 3.09 (m, 2H), 3.06 – 2.97 (m, 2H). 13C NMR (75 MHz, DMSO-d6) δ 152.5, 151.3, 149.2,
146.1, 127.3, 125.8, 125.3, 122.9, 122.1, 115.7, 115.5, 114.8, 108.8, 107.1, 56.6, 56.2, 45.9, 43.7, 26.4
159
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Multi-step reaction with 5 steps 1.1: sodium hydride / DMFA / 0.28 h / 0 °C 1.2: 3 h / 100 °C 2.1: polyphosphoric acid / chlorobenzene / 1.33 h / 130 °C 3.1: magnesium; 1,2-dibromoethane / tetrahydrofuran / 1.5 h / 80 °C 3.2: 0.5 h / 0 - 20 °C 4.1: triethylamine / ethanol 5.1: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160368 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
160
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Multi-step reaction with 4 steps 1.1: polyphosphoric acid / chlorobenzene / 1.33 h / 130 °C 2.1: magnesium; 1,2-dibromoethane / tetrahydrofuran / 1.5 h / 80 °C 2.2: 0.5 h / 0 - 20 °C 3.1: triethylamine / ethanol 4.1: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160373 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
161
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Multi-step reaction with 3 steps 1.1: magnesium; 1,2-dibromoethane / tetrahydrofuran / 1.5 h / 80 °C 1.2: 0.5 h / 0 - 20 °C 2.1: triethylamine / ethanol 3.1: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160377 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
162
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Multi-step reaction with 2 steps 1: triethylamine / ethanol 2: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160381 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
163
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Multi-step reaction with 5 steps 1.1: potassium carbonate / DMFA / 5 h / 20 °C 2.1: polyphosphoric acid / chlorobenzene / 4.33 h / 130 °C 3.1: magnesium; 1,2-dibromoethane / tetrahydrofuran / 1.5 h / 80 °C 3.2: 0 - 20 °C 4.1: triethylamine / ethanol 5.1: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160382 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
164
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Multi-step reaction with 4 steps 1.1: polyphosphoric acid / chlorobenzene / 4.33 h / 130 °C 2.1: magnesium; 1,2-dibromoethane / tetrahydrofuran / 1.5 h / 80 °C 2.2: 0 - 20 °C 3.1: triethylamine / ethanol 4.1: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160385 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
165
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Synthesize Find similar
Rx-ID: 40160388 Find similar reactions
Multi-step reaction with 3 steps 1.1: magnesium; 1,2-dibromoethane / tetrahydrofuran / 1.5 h / 80 °C 1.2: 0 - 20 °C 2.1: triethylamine / ethanol 3.1: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
166
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Stage #1: With sodium tetrahydroborate; ethanol
0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
Hide Experimental Procedure
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Rx-ID: 40160316 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
4.1. General procedure for the synthesis of N-benzylatedphenethylamines 1b–u
General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products. N-((1H-benzo[d]imidazol-7-yl)methyl)-2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (1f); Obtained from 2C-B·HCl and 4 by general procedure A in 72percent yield as a colorless solid. mp. 256 – 258 °C. 1H NMR (300 MHz, DMSO-d6) δ 9.82 (br s, 2H), 9.75 (s, 1H), 7.91–7.84 (m, 2H), 7.59 (dd, J = 8.0, 7.8 Hz, 1H), 7.16 (s, 1H), 7.04 (s, 1H), 4.71 (s, 2H),
3.78 (s, 3H), 3.73 (s, 3H), 3.31 – 3.19 (m, 2H), 3.07 – 2.96 (m, 2H). 13C NMR (75 MHz, DMSO-d6) δ 151.3, 149.2, 140.2, 130.8, 130.7, 128.3, 125.8, 125.3, 119.0, 115.7, 115.1, 114.8,
108.7, 56.6, 56.3, 45.9, 45.3, 26.5
167
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Stage #1: With sodium tetrahydroborate; ethanol
0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
Hide Experimental Procedure
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Rx-ID: 40160317 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
4.1. General procedure for the synthesis of N-benzylatedphenethylamines 1b–u
General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was
then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products. N-((1H-indazol-7-yl)methyl)-2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (1g); Obtained from 2C-B·HCl and 5 by general procedure A in 80percent yield as a colorless solid. mp. 207 – 209 °C. 1H NMR (300 Mhz, DMSO-d6) δ 9.60 (br s, 2H), 8.14 (s, 1H), 7.80 (d, J = 8.1 Hz, 1H), 7.59 (d, J = 7.0 Hz, 1H), 7.15 (s, 1H), 7.14 (dd, J = 8.0, 7.1 Hz, 1H),
7.00 (s, 1H), 4.55 (s, 2H), 3.77 (s, 3H), 3.70 (s, 3H), 3.24 – 3.11 (m, 2H), 3.04 – 2.94 (m, 2H). 13C NMR (75 MHz, DMSO-d6) δ 151.3, 149.2, 139.2, 133.7, 128.5, 125.4, 123.2, 121.6, 120.2, 115.8, 114.8, 114.3, 108.8, 56.6, 56.2, 46.2, 45.9, 26.6
168
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Multi-step reaction with 9 steps 1: ammonium hydroxide / water / 0 °C 2: bromine; potassium hydroxide / water / 0 - 60 °C 3: hydrogen; palladium 10 on activated carbon / methanol / 760.05 Torr 4: hydrochlorid acid / water / 2 h / |Reflux 5: sulfuric acid / |Reflux 6: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 1 h 7: manganese(IV) oxide / DMFA; dichloromethane / 4 h / 20 °C 8: triethylamine / ethanol 9: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160390 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
169
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Multi-step reaction with 8 steps 1: bromine; potassium hydroxide / water / 0 - 60 °C 2: hydrogen; palladium 10 on activated carbon / methanol / 760.05 Torr 3: hydrochlorid acid / water / 2 h / |Reflux 4: sulfuric acid / |Reflux 5: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 1 h 6: manganese(IV) oxide / DMFA; dichloromethane / 4 h / 20 °C 7: triethylamine / ethanol 8: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160396 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
170
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Multi-step reaction with 7 steps 1: hydrogen; palladium 10 on activated carbon / methanol / 760.05 Torr 2: hydrochlorid acid / water / 2 h / |Reflux 3: sulfuric acid / |Reflux 4: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 1 h 5: manganese(IV) oxide / DMFA; dichloromethane / 4 h / 20 °C 6: triethylamine / ethanol 7: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160401 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
171
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Multi-step reaction with 6 steps 1: hydrochlorid acid / water / 2 h / |Reflux 2: sulfuric acid / |Reflux 3: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 1 h 4: manganese(IV) oxide / DMFA; dichloromethane / 4 h / 20 °C 5: triethylamine / ethanol 6: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160406 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
172
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Rx-ID: 40160411 Find similar reactions
Multi-step reaction with 5 steps 1: sulfuric acid / |Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 1 h 3: manganese(IV) oxide / DMFA; dichloromethane / 4 h / 20 °C 4: triethylamine / ethanol 5: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
173
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Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 1 h 2: manganese(IV) oxide / DMFA; dichloromethane / 4 h / 20 °C 3: triethylamine / ethanol 4: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160414 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
174
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175
Multi-step reaction with 3 steps 1: manganese(IV) oxide / DMFA; dichloromethane / 4 h / 20 °C 2: triethylamine / ethanol 3: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160417 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
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Multi-step reaction with 2 steps 1: triethylamine / ethanol 2: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160419 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
176
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Multi-step reaction with 9 steps 1.1: hydrochlorid acid; hydroxylamine hydrochloride; sodium sulfate / water / 55 °C 2.1: sulfuric acid / neat (no solvent) / 55 - 80 °C 3.1: sodium hydroxide; hydrogen peroxide; potassium chloride / water / 2.25 h / 0 - 20 °C 4.1: methanol; hexane / 0.5 h 5.1: sodium nitrite; tetrafluoroboric acid / water / 1 h / 0 - 20 °C 5.2: 1 h 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h 7.1: manganese(IV) oxide / DMFA; dichloromethane / 20 °C 8.1: triethylamine / ethanol 9.1: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160420 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
177
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Synthesize Find similar
Rx-ID: 40160426 Find similar reactions
Multi-step reaction with 8 steps 1.1: sulfuric acid / neat (no solvent) / 55 - 80 °C 2.1: sodium hydroxide; hydrogen peroxide; potassium chloride / water / 2.25 h / 0 - 20 °C 3.1: methanol; hexane / 0.5 h 4.1: sodium nitrite; tetrafluoroboric acid / water / 1 h / 0 - 20 °C 4.2: 1 h 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h 6.1: manganese(IV) oxide / DMFA; dichloromethane / 20 °C 7.1: triethylamine / ethanol 8.1: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
178
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Multi-step reaction with 7 steps 1.1: sodium hydroxide; hydrogen peroxide; potassium chloride / water / 2.25 h / 0 - 20 °C 2.1: methanol; hexane / 0.5 h 3.1: sodium nitrite; tetrafluoroboric acid / water / 1 h / 0 - 20 °C 3.2: 1 h 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h 5.1: manganese(IV) oxide / DMFA; dichloromethane / 20 °C 6.1: triethylamine / ethanol 7.1: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160432 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
179
Synthesize Find similar
Multi-step reaction with 6 steps 1.1: methanol; hexane / 0.5 h 2.1: sodium nitrite; tetrafluoroboric acid / water / 1 h / 0 - 20 °C 2.2: 1 h 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h 4.1: manganese(IV) oxide / DMFA; dichloromethane / 20 °C 5.1: triethylamine / ethanol
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Rx-ID: 40160438 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
6.1: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
180
Synthesize Find similar
Multi-step reaction with 5 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 1 h / 0 - 20 °C 1.2: 1 h 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h 3.1: manganese(IV) oxide / DMFA; dichloromethane / 20 °C 4.1: triethylamine / ethanol 5.1: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160444 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
181
Synthesize Find similar
182
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h 2: manganese(IV) oxide / DMFA; dichloromethane / 20 °C 3: triethylamine / ethanol 4: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160448 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
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Multi-step reaction with 3 steps 1: manganese(IV) oxide / DMFA; dichloromethane / 20 °C 2: triethylamine / ethanol 3: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160452 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
183
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Multi-step reaction with 2 steps 1: triethylamine / ethanol 2: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160455 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
184
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Rx-ID: 37779829 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 20 °C 2: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C View Scheme
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Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
185
Synthesize
Synthesize
Rx-ID: 37779924
Find similar With sodium tetrahydroborate in ethanol
T=20°C; 0.5 h;
Find similar
Find similar reactions
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
186
Synthesize Find similar Stage #1: With sodium tetrahydroborate; ethanol
0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
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Rx-ID: 40160315 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
Hide Experimental Procedure
4.1. General procedure for the synthesis of N-benzylatedphenethylamines 1b–u
General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products. 2-(4-bromo-2,5-dimethoxyphenyl)-N-((2,3-dihydrobenzofuran-7-yl)methyl)ethanamine hydrochloride (1e); Obtained from 2C-B·HCl and 2,3-dihydrobenzofuran-7-carbaldehyde by general procedure A in 73percent yield as a colorless solid. mp. 208 – 210 °C. 1H NMR (300 Mhz, DMSO-d6) δ 9.51 (br s, 2H), 7.36 (dd, J = 7.5, 0.9 Hz, 1H), 7.25 (dd, J = 7.3, 0.9 Hz, 1H),
7.17 (s, 1H), 7.01 (s, 1H), 6.85 (dd, J = 7.5, 7.3 Hz, 1H), 4.56 (t, J = 8.7 Hz, 2H), 4.04 (s, 2H), 3.78 (s, 3H), 3.73 (s, 3H), 3.21 (t, J = 8.7 Hz, 2H), 3.12 – 2.92 (m, 4H). 13C NMR (75 MHz, DMSO-d6) δ 158.2, 151.3, 149.2, 129.2, 127.4, 125.7, 125.3, 120.3, 115.7, 114.8, 112.9, 108.7, 71.3, 56.6, 56.2, 45.5, 44.0, 29.2, 26.4
187
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Rx-ID: 40160332 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol 2: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
188
Synthesize Find similar With borane in tetrahydrofuran
18 h; Heating;
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Rx-ID: 4004889 Find similar reactions
Glennon; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis
Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 1929 - 1935 Title/Abstract Full Text View citing articles Show Details
189
Synthesize Find similar Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 4h 2: BH3 / tetrahydrofuran / 18 h / Heating View Scheme
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Rx-ID: 18234310 Find similar reactions
Glennon; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis
Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 1929 - 1935 Title/Abstract Full Text View citing articles Show Details
190
Synthesize Find similar Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 4h 2: BH3 / tetrahydrofuran / 18 h / Heating View Scheme
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Rx-ID: 18239491 Find similar reactions
Glennon; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis
Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 1929 - 1935 Title/Abstract Full Text View citing articles Show Details
191
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Stage #1: With sodium tetrahydroborate; ethanol
0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
Hide Experimental Procedure
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Rx-ID: 40160328 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
4.1. General procedure for the synthesis of N-benzylatedphenethylamines 1b–u
General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products. 2-((4-bromo-2,5-dimethoxyphenethylamino)methyl)-6-methoxyphenol hydrochloride (1s); Obtained from 2C-B·HCl and 2-hydroxy-3-methoxybenzaldehyde by general procedure A in 69percent yield as an off-white solid. mp. 205 – 206 °C. 1H NMR (300 MHz, DMSO-d6) δ 9.31 (br s, 2H), 7.16 (s, 1H), 7.05 (dd, J = 7.7, 1.3 Hz, 1H), 6.99 (dd, J = 8.1, 1.3 Hz, 1H), 6.99 (s,
1H), 6.80 (dd, J = 8.1, 7.7 Hz, 1H), 4.09 (s, 2H), 3.81 (s, 3H), 3.78 (s, 3H), 3.73 (s, 3H), 3.09 – 2.91 (m, 4H). 13C NMR (75 MHz, DMSO-d6) δ 151.3, 149.2, 147.5, 144.9, 125.4, 122.9, 118.9, 118.5, 115.7, 114.8, 112.4, 108.7, 56.6, 56.2, 55.9, 45.6, 44.4, 26.4
192
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Rx-ID: 40160351 Find similar reactions
193
Multi-step reaction with 2 steps 1: triethylamine / ethanol 2: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
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Stage #1: With sodium tetrahydroborate; ethanol
0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
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Rx-ID: 40160327 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
4.1. General procedure for the synthesis of N-benzylatedphenethylamines 1b–u
General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products. 2-(4-bromo-2,5-dimethoxyphenyl)-N-(2-fluoro-3-methoxybenzyl)ethanamine hydrochloride (1r); Obtained from 2C-B·HCl and 2-fluoro-3-methoxybenzaldehyde by general procedure A in 72percent yield as a colorless solid. mp. 170 – 171 °C. 1H NMR (300 MHz, DMSO-d6) δ 9.68 (br s, 2H), 7.31 – 7.14 (m, 3H), 7.17 (s, 1H), 7.02 (s, 1H), 4.18 (s, 2H), 3.85 (s, 3H), 3.78 (s,
3H), 3.74 (s, 3H), 3.17 – 2.94 (m, 4H). 13C NMR (75 MHz, DMSO) δ 151.5, 150.1 (d, 1JCF = 247.2 Hz), 149.3, 147.2 (d, 2JCF = 10.4 Hz), 125.4, 124.5 (d, 3JCF = 4.6 Hz), 122.8, 119.8 (d,2JCF = 11.8 Hz), 115.8, 115.0, 114.5, 108.9, 56.6, 56.2, 56.2, 45.9, 42.7 (d, 3JCF = 4.8 Hz), 26.3
194
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Rx-ID: 43732272 Find similar reactions
64%
Stage #1: With triethylamine in ethanol
Stage #2: With sodium tetrahydroborate in ethanol
0.5 h; Stage #3: With hydrogenchloride in diethyl ether; ethyl acetate
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Petersen, Ida Nymann; Villadsen, Jonas; Hansen, Hanne Demant; Jensen, Anders A.; Lehel, Szabolcs; Gillings, Nic; Herth, Matthias M.; Knudsen, Gitte M.; Kristensen, Jesper L.
Bioorganic and Medicinal Chemistry, 2016 , vol. 24, # 21 p. 5353 - 5356 Title/Abstract Full Text Show Details
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General procedure A reductive animation
General procedure: The amine (1 eq and aldehyde (1,1 eq) was dissolved in EtOH (0.5 mmol/ml) and added a drop of Et3N. When TLC indicated full conversion to the imine (1-48 h), NaBH4 (2 eq) was added and the mixture was further stirred for 30 min. The volume was reduced and the mixture was added water and extracted with DCM, evaporated on celite and purified in flash column chromatography (5 percent Et3N in EtOAc), redissolved in EtOAc participated as the HCl salt using 2 M HCl in diethyl ether (Sigma Aldrich).
195
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Rx-ID: 40160314
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0.167 g
Stage #1: With sodium tetrahydroborate; ethanol
0.5 h; Stage #2: With oxalic acid in diethyl ether; ethanol
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Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
N-(benzo[d]oxazol-7-ylmethyl)-2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hemioxalate (1d)
To a suspension of 2C-B·HCl (0.178 g, 0.6 mmol) and 6 (0.103 g, 0.7 mmol) in EtOH (10 mL) was added Et3N (0.6 mmol) and the reaction was stirred until formation of the imine was complete according to TLC or GC (3 hours). NaBH4 (1.2 mmol) was added to the reaction which was stirred for another 30 minutes. The reaction mixture was evaporated under reduced pressure and redissolved in EtOAc/H2O (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with EtOAc (2 × 15 mL). The combined organic extracts were dried (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by radial chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and dripped slowly into a saturated solution of oxalic acid in Et2O (10 mL). The formed precipitate was isolated by filtration and recrystallized from EtOH to give the title compound, 1d (0.167 g, 58percent) as tan crystals. mp. 201 °C dec. 1H NMR (300 Mhz, DMSO-d6) δ 9.53 (br s, 3H), 8.83 (s, 1H), 7.83 (d, J = 7.8 Hz, 1H), 7.60 (d, J = 7.4 Hz, 1H), 7.45 (dd, J = 7.8, 7.4
Hz, 1H), 7.16 (s, 1H), 6.98 (s, 1H), 4.46 (s, 1H), 3.77 (s, 2H), 3.72 (s, 1H), 3.20 – 3.11 (m, 1H), 2.97 – 2.88 (m, 1H). 13C NMR (75 MHz, DMSO-d6) δ 164.4 (2C, oxalate), 154.1, 151.3,
149.2, 148.1, 139.6, 126.8, 125.5, 124.7, 120.6, 116.5, 115.7, 114.9, 108.7, 56.6, 56.2, 46.2, 44.2, 26.8
196
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Rx-ID: 37779835 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 20 °C 2: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C View Scheme
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Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
197
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With sodium tetrahydroborate in ethanol
T=20°C; 0.5 h;
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Rx-ID: 37779927 Find similar reactions
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
198
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0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
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Rx-ID: 40160313 Find similar reactions
Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard
Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details
Hide Experimental Procedure
4.1. General procedure for the synthesis of N-benzylatedphenethylamines 1b–u
General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products. N-(benzo[b]thiophen-7-ylmethyl)-2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (1c); Obtained from 2C-B·HCl and 3 by general procedure A in 55percent yield as fluffy colorless crystals. mp. 219 – 220 °C. 1H NMR (300 MHz, DMSO-d6) δ 9.64 (br s, 1H), 7.92 (d, J = 7.8 Hz, 1H), 7.80 (d, J = 5.4 Hz, 1H), 7.70 (d, J = 7.2 Hz, 1H), 7.53 (d, J = 5.4 Hz,
1H), 7.47 (dd, J = 7.8, 7.2 Hz, 1H), 7.14 (s, 1H), 7.01 (s, 1H), 4.41 (s, 2H), 3.79 (s, 3H), 3.73 (s, 3H), 3.28 – 3.15 (m, 2H), 3.08 – 2.94 (m, 2H). 13C NMR (75 MHz, DMSO-d6) δ 151.3, 149.2, 139.9, 139.3, 127.1, 126.1, 125.1, 125.0, 124.5 (2C), 124.1, 115.6, 114.8, 108.9, 56.6, 56.1, 48.7, 46.4, 26.5
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