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199
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Rx-ID: 40160358 Find similar reactions
Multi-step reaction with 2 steps 1: triethylamine / ethanol 2: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
200
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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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Rx-ID: 7779342 Find similar reactions
Mescalin, entspr. Aldehyd, H2;
Hexachimie
Patent: FR2328457 , 1977 ; Chem.Abstr., vol. 88, # 74105 Full Text Show Details
201
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0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
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Rx-ID: 40160324 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 products2-(4-bromo-2,5-dimethoxyphenyl)-N-(2,3-dimethoxybenzyl)ethanamine hydrochloride (1n); Obtained from 2C-B·HCl and 2,3-dimethoxybenzaldehyde by general procedure A in 69percent yield as a colorless solid. mp. 119 – 120 °C. 1H NMR (300 MHz, DMSO-d6) δ 9.50 ( br s, 2H), 7.23 – 7.16 (m, 2H), 7.12 – 1.08 (m, 2H), 7.01 (s, 1H), 4.12 (s, 2H), 3.82 (s, 3H), 3.79 (s, 3H), 3.79 (s, 3H) 3. 3.73 (s, 3H), 3.12 – 2.94 (m, 4H). 13C NMR (75 MHz, DMSO-d6) δ 152.0, 151.3, 149.2, 146.9, 125.4, 125.2, 124.0,
122.2, 115.7, 114.8, 113.6, 108.7, 60.5, 56.6, 56.2, 55.8, 45.8, 44.1, 26.3
202
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: 40160325 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-(2,4-dimethoxybenzyl)ethanamine hydrochloride (1o); Obtained from 2C-B·HCl and 2,4-dimethoxybenzaldehyde by general procedure A in 88percent yield as a colorless solid. mp. 167 – 168 °C. 1H NMR (300 MHz, DMSO-d6) δ 9.29 (br s, 1H), 7.41 (d, J = 8.3 Hz, 1H), 7.16 (s, 1H), 7.00 (s, 1H), 6.60 (d, J = 2.3 Hz, 1H), 6.54 (dd, J = 8.3, 2.3 Hz, 1H), 4.02 (s,2H), 3.81 (s, 3H), 3.78 (s, 3H), 3.77 (s,3H), 3.73 (s, 3H), 2.98 (s, 4H). 13C NMR (75 MHz, DMSO-d6) δ 161.3,
158.5, 151.3, 149.2, 132.4, 125.5, 115.7, 114.8, 111.7, 108.7, 104.8, 98.2, 56.6, 56.2, 55.7, 55.4, 45.2, 44.2, 26.3
203
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0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
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Rx-ID: 40160326 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-(2,6-dimethoxybenzyl)ethanamine hydrochloride (1q); Obtained from 2C-B·HCl and 2,6-dimethoxybenzaldehyde by general procedure A in 56percent yield as a colorless solid. mp. 193 – 194 °C. 1H NMR (300 MHz, DMSO-d6) δ 9.07 (br s, 2H), 7.36 (t, J = 8.4 Hz, 1H), 7.16 (s, 1H), 6.97 (s, 1H), 6.71 (d, J = 8.4 Hz, 2H), 4.08 (s, 2H), 3.81 (s, 6H), 3.78 (s, 3H), 3.73 (s, 3H), 2.97 (s, 4H). 13C NMR (75 MHz, DMSO-d6) δ 158.4 (2C), 151.2, 149.2, 131.1, 125.4, 115.7, 114.7,
108.7, 106.9, 103.8 (2C), 56.6, 56.2, 55.9 (2C), 45.5, 38.6, 26.3
204
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0.5 h; Stage #2: With hydrochlorid acid in diethyl ether; ethanol
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Rx-ID: 40160331 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-(2,5-dimethoxybenzyl)ethanamine hydrochloride (1p); Obtained from 2C-B·HCl and 2,5-dimethoxybenzaldehyde by general procedure A in 71percent yield as a colorless solid. mp. 150 – 151 °C. 1H NMR (300 MHz, DMSO-d6) δ 9.41 (br s, 2H), 7.23 (d, J = 2.9 Hz, 1H), 7.17 (s, 1H), 7.01 (s, 1H), 6.99 (d, J = 9.0 Hz, 1H), 6.93 (dd, J = 9.0, 2.9 Hz, 1H), 4.08 (s, 2H), 3.79 (s, 3H), 3.76 (s, 3H), 3.73 (s, 3H), 3.72 (s, 3H), 3.10 – 2.93 (m, 4H). 13C NMR (75 MHz, DMSO-d6) δ
152.7, 151.3, 151.2, 149.2, 125.4, 120.4, 117.1, 115.7, 114.9, 114.8, 111.9, 108.7, 56.6, 56.2, 56.0, 55.5, 45.6, 44.4, 26.3
205
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Rx-ID: 40160342 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
206
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Rx-ID: 40160344 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
207
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Rx-ID: 40160346 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
208
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Rx-ID: 40160348 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
209
Synthesize Find similar Multi-step reaction with 3 steps 1: methanol / 5 h / |Reflux 2: triethylamine / ethanol 3: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160305 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
210
Synthesize Find similar Multi-step reaction with 2 steps 1: triethylamine / ethanol 2: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160310 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
211
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: 40160320 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-methoxypyridin-3-yl)methyl)ethanamine, dihydrochloride (1j); Obtained from 2C-B·HCl and 8 by general procedure A in 69percent yield as a colorless solid. mp. 201 – 202 °C. 1H NMR (300 Mhz, DMSO-d6) δ 9.74 (br s, 1H), 9.59 (br s, 2H), 8.18 (dd, J = 5.0, 1.8 Hz, 1H), 7.97 (dd, J = 7.3, 1.8 Hz, 1H), 7.17 (s, 1H), 7.04 (dd, J = 7.3, 5.0 Hz, 1H), 7.02 (s, 1H), 4.10 (t, J = 5.6 Hz, 2H), 3.90 (s, 3H), 3.78 (s, 3H), 3.74 (s, 3H), 3.15 – 2.94 (m, 3H). 13C NMR (75 MHz, DMSO-d6) δ 161.2, 151.3, 149.2, 147.3, 140.4, 125.4, 116.9, 115.7, 114.9, 114.5, 108.8, 56.6, 56.3, 53.6, 45.9, 44.2
212
Synthesize Find similar 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: methanol / 5 h / |Reflux 3.1: triethylamine / ethanol 4.1: sodium tetrahydroborate; ethanol / 0.5 h View Scheme
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Rx-ID: 40160365 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
A
213
B
C
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Rx-ID: 27956807 Find similar reactions
B: 43 mg
Stage #1: With sodium hydride in N,N-dimethylformamide
Stage #2: With hydrogenchloride in methanol
T=20°C; 12 h; Further stages.;
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Nichols, David E.; Frescas, Stewart P.; Chemel, Benjamin R.; Rehder, Kenneth S.; Zhong, Desong; Lewin, Anita H.
Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 11 p. 6116 - 6123 Title/Abstract Full Text View citing articles Show Details
214
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0.5 h; Cooling with ice; Stage #2: With hydrogenchloride in ethanol
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Rx-ID: 40376255 Find similar reactions
Nichols, David E.; Sassano, M. Flori; Halberstadt, Adam L.; Klein, Landon M.; Brandt, Simon D.; Elliott, Simon P.; Fiedler, Wolfgang J.
ACS Chemical Neuroscience, 2015 , vol. 6, # 7 p. 1165 - 1175 Title/Abstract Full Text View citing articles Show Details
215
Synthesize Find similar Stage #1: With sodium tetrahydroborate in methanol
0.5 h; Cooling with ice; Stage #2: With hydrogenchloride in ethanol
216
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Rx-ID: 40376258 Find similar reactions
Nichols, David E.; Sassano, M. Flori; Halberstadt, Adam L.; Klein, Landon M.; Brandt, Simon D.; Elliott, Simon P.; Fiedler, Wolfgang J.
ACS Chemical Neuroscience, 2015 , vol. 6, # 7 p. 1165 - 1175 Title/Abstract Full Text View citing articles Show Details
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Synthesize Find similar Stage #1: With sodium tetrahydroborate in methanol
0.5 h; Cooling with ice; Stage #2: With hydrogenchloride in ethanol
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Rx-ID: 40376259 Find similar reactions
Nichols, David E.; Sassano, M. Flori; Halberstadt, Adam L.; Klein, Landon M.; Brandt, Simon D.; Elliott, Simon P.; Fiedler, Wolfgang J.
ACS Chemical Neuroscience, 2015 , vol. 6, # 7 p. 1165 - 1175 Title/Abstract Full Text View citing articles Show Details
217
Synthesize Find similar With borane in tetrahydrofuran
18 h; Heating;
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Rx-ID: 4004890 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
218
Synthesize Find similar Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 4 h 2: BH3 / tetrahydrofuran / 18 h / Heating View Scheme
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Rx-ID: 18234311 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
219
Synthesize Find similar Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 4 h 2: BH3 / tetrahydrofuran / 18 h / Heating View Scheme
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Rx-ID: 18261587 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
220
Synthesize Find similar Stage #1: With sodium tetrahydroborate in methanol
24 h; Stage #2: With hydrogenchloride in isopropyl alcohol
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Rx-ID: 39258118 Find similar reactions
Tirapegui, Cristian; Toro-Sazo, Miguel A.; Cassels, Bruce K.
Journal of the Chilean Chemical Society, 2014 , vol. 59, # 3 p. 2625 - 2627 Title/Abstract Full Text View citing articles Show Details
Hide Experimental Procedure
General procedure for the preparation of N-benzylated 2-arylethanamine hydrochlorides.
General procedure: The appropriate amine (5.5 mmol) andaldehyde (6.0 mmol) were dissolved in MeOH (90 mL) and stirred overnight at room temperature. Powdered NaBH4 (24 mmol) was then added in small portions, with good stirring, over approximately 30 min, and the reaction was allowed to proceed for 24 h. The solvent was removed in a rotary evaporator and the cream-colored to light yellow residue was taken up with CH2Cl2 (50mL) and washed with saturated aqueous NaHCO3 solution. The organic phase was dried (Na2SO4), filtered, and concentrated to dryness. The light yellow oil was dissolved in 2-propanol (5 mL) to which was added 37percent HCl (540 mL),and the solution was diluted with Et2O (100 mL) to afford the salt, usually as a white crystalline powder.
221
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Rx-ID: 43732273 Find similar reactions
63%
Stage #1: With triethylamine in ethanol
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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.
Stage #2: With sodium tetrahydroborate in ethanol
0.5 h; Stage #3: With hydrogenchloride in diethyl ether; ethyl acetate
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).
222
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With sodium tetrahydroborate in ethanol
T=20°C; 4 h;
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Rx-ID: 27956802 Find similar reactions
Nichols, David E.; Frescas, Stewart P.; Chemel, Benjamin R.; Rehder, Kenneth S.; Zhong, Desong; Lewin, Anita H.
Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 11 p. 6116 - 6123 Title/Abstract Full Text View citing articles Show Details
223
Synthesize Find similar Mescalin, entspr. Aldehyd, H2;
Rx-ID: 7781223 Find similar reactions
Hexachimie
Patent: FR2328457 , 1977 ; Chem.Abstr., vol. 88, # 74105 Full Text Show Details
224
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Synthesize Find similar
Rx-ID: 40376260 Find similar reactions
Stage #1: With sodium tetrahydroborate in methanol
0.5 h; Cooling with ice; Stage #2: With hydrogenchloride in ethanol
Nichols, David E.; Sassano, M. Flori; Halberstadt, Adam L.; Klein, Landon M.; Brandt, Simon D.; Elliott, Simon P.; Fiedler, Wolfgang J.
ACS Chemical Neuroscience, 2015 , vol. 6, # 7 p. 1165 - 1175 Title/Abstract Full Text View citing articles Show Details
225
Synthesize Find similar Stage #1: With sodium tetrahydroborate in methanol
0.5 h; Cooling with ice; Stage #2: With hydrogenchloride in ethanol
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Rx-ID: 40376261 Find similar reactions
Nichols, David E.; Sassano, M. Flori; Halberstadt, Adam L.; Klein, Landon M.; Brandt, Simon D.; Elliott, Simon P.; Fiedler, Wolfgang J.
ACS Chemical Neuroscience, 2015 , vol. 6, # 7 p. 1165 - 1175 Title/Abstract Full Text View citing articles Show Details
226
Synthesize Find similar Stage #1: With sodium tetrahydroborate in methanol
0.5 h; Cooling with ice; Stage #2: With hydrogenchloride in ethanol
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Rx-ID: 40376262 Find similar reactions
Nichols, David E.; Sassano, M. Flori; Halberstadt, Adam L.; Klein, Landon M.; Brandt, Simon D.; Elliott, Simon P.; Fiedler, Wolfgang J.
ACS Chemical Neuroscience, 2015 , vol. 6, # 7 p. 1165 - 1175 Title/Abstract Full Text View citing articles Show Details
227
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Rx-ID: 41708104 Find similar reactions
Multi-step reaction with 2 steps 1: pyridine / 20 °C 2: dichloromethane / 0 - 20 °C View Scheme
Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan
Patent: EP2950104 A1, 2015 ; Title/Abstract Full Text Show Details
228
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Rx-ID: 41708106 Find similar reactions
in dichloromethane
T=0 - 20°C; Hide Experimental Procedure
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Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan
Patent: EP2950104 A1, 2015 ; Location in patent: Page/Page column 0012; 0072 ; Title/Abstract Full Text Show Details
9:Example 9
Example 9 Preparation of N-(2-methoxybenzyl)-2-(2, 5-dimethoxy-4-succinamidophenyl)ethylamine TFA salt (Hapten-2) To a cooled solution of N-(tert-Butoxycarbonyl)-N-(2-methoxybenzyl)-2-(2, 5-dimethoxy-4-succinamidophenyl)ethylamine 8 (800 mg, 0.0015 mol) in dichloromethane (10 ml) at 0 °C was added trifluoroacetic acid (10 ml) and the mixture was left stirring at room temperature overnight. The solvent was removed under vacuum and then was triturated several times with Et2O to give the (Hapten-2).
229
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Rx-ID: 23188456 Find similar reactions
Iyengar, Rajesh R.; Judd, Andrew S.; Zhao, Gang; Kym, Philip R.; Sham, Hing L.; Gu, Yugui; Liu, Gang; Liu, Mei; Zhao, Hongyu; Clark, Richard F.; Frevert, Ernst U.; Cool, Barbara L.; Zhang, Tianyuan; Keyes, Robert F.; Hansen, Todd M.; Xin, Zhili
Patent: US2005/38068 A1, 2005 ; Location in patent: Page/Page column 36 ; Title/Abstract Full Text Show Details
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