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References
1
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With ammonium hydroxide
Erhitzen des Reaktionsprodukts mit wss. HCl;
Rx-ID: 326982 Find similar reactions
McCord et al.
Journal of the American Chemical Society, 1957 , vol. 79, p. 5693,5696 Full Text View citing articles Show Details
2
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Rx-ID: 2821311
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acid hydrolysis;
Asher, Vikram; Becu, Christian; Anteunis, Marc J. O.; Callens, Roland
Tetrahedron Letters, 1981 , vol. 22, p. 141 - 144 Title/Abstract Full Text View citing articles Show Details
Stage #1: With sodium hydroxide
T=20°C; 3 h; Stage #2: With hydrogenchloride
T=16°C; 100 h;
Zink, Charles N.; Kim, Hyun-Joong; Fishbein, James C.
Journal of Organic Chemistry, 2006 , vol. 71, # 1 p. 202 - 209 Title/Abstract Full Text View citing articles Show Details
3
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With triethylamine in methanol
T=64°C; 7 h;
Rx-ID: 3727693 Find similar reactions
Kogami; Okawa
Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 8 p. 2963 - 2965 Title/Abstract Full Text View citing articles Show Details
4
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With triethylamine in methanol
T=64°C; 7 h;
Rx-ID: 3727694 Find similar reactions
Kogami; Okawa
Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 8 p. 2963 - 2965 Title/Abstract Full Text View citing articles Show Details
5
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Rx-ID: 10212295 Find similar reactions
With Pseudomonas putida N-methyl-L-amino acid dehydrogenase; T. viride L-lysine oxidase; Tris buffer; Adenine-flavine dinucleotide; catalase in various solvent(s) T=30°C; pH=8.2; 72 h;
Yasuda, Mari; Ueda, Makoto; Muramatsu, Hisashi; Mihara, Hisaaki; Esaki, Nobuyoshi
Tetrahedron Asymmetry, 2006 , vol. 17, # 12 p. 1775 - 1779 Title/Abstract Full Text View citing articles Show Details
6
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Multi-step reaction with 2 steps 1: 77 percent / H2 / Pd black / methanol / 0.5 h 2: 97.3 percent / Et3N / methanol / 7 h / 64 °C View Scheme
Rx-ID: 18335369 Find similar reactions
Kogami; Okawa
Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 8 p. 2963 - 2965 Title/Abstract Full Text View citing articles Show Details
7
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Multi-step reaction with 2 steps 1: H2 / Pd black / methanol / 0.5 h 2: Et3N / methanol / 7 h / 64 °C View Scheme
Rx-ID: 18335370 Find similar reactions
Kogami; Okawa
Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 8 p. 2963 - 2965 Title/Abstract Full Text View citing articles Show Details
8
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T=20°C; 5 h;
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Rx-ID: 37195339 Find similar reactions
Blizzard, Timothy A.; Singh, Sanjay; Patil, Basanagoud; Chidurala, Naresh; Komanduri, Venukrishnan; Debnath, Samarpita; Belyakov, Sergei; Crespo, Alejandro; Struck, Alice; Kurtz, Marc; Wiltsie, Judyann; Shen, Xun; Sonatore, Lisa; Arocho, Marta; Lewis, Dale; Ogletree, Martin; Biftu, Tesfaye
Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 4 p. 1111 - 1115
Title/Abstract Full Text View citing articles Show Details
9
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Rx-ID: 37340387 Find similar reactions
With potassium carbonate in ethanol
T=25°C; 16 h; Hide Experimental Procedure
SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; LIU, Xinchang; SIEGFRIED, Goldmann
Patent: WO2014/29193 A1, 2014 ; Location in patent: Paragraph 00236; 00238 ; Title/Abstract Full Text Show Details
30:[00236] Example 28:(38)_4_((6-(2-bromo_4-fhiorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydrOpYri midin-4-yI)methyl)morpholine-3-carboxylic acid
General procedure: [00236] Example 28:(38)_4_((6-(2-bromo_4-fhiorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydrOpYri midin-4-yI)methyl)morpholine-3-carboxylic acid A mixture of ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1 ,4dihydropyrimidine-5-carboxylate (7.7 g, 15.3 mmol), (S)-morpholine-3-carboxylic acid (2 g, 15.3 mmol) and potassium carbonate (4.23 g, 30.6 mmol) in anhydrous ethanol (154 mL)was stirred at 25 C for 16 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (V/V) 25/1) to give the title compound as a yellow solid (7.26 g, 86percent). The compound was characterized by the following spectroscopic data:MS-ESI: (ESI, pos.ion) m/z: 553.2 [M+ljH NMR (400 M1-lz, DMSO-d6): 12.90 (s, 111), 9.84 (s, 11-1), 8.04 (d, IH), 7.95 (d, IH),7.57-7.55 (m, 111), 7.43-7.37 (m, IH), 7.23-7J9 (m, 11-1), 6.03 (s, IH), 4.30-3.92 (m, 5H),3.84-3.82 (m, IH), 3.74-3.52 (m, 3H), 3.11-3.07 (m, IH), 2.55-2.39 (m, IH), 1.06 (t, 311).
10
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Stage #1: With lithium hydroxide hydrate in methanol; water
T=20°C; 2 h; Stage #2: T=20°C; 2 h;
Rx-ID: 29523869 Find similar reactions
Laars, Marju; Raska, Henri; Lopp, Margus; Kanger, Tonis
Tetrahedron Asymmetry, 2010 , vol. 21, # 5 p. 562 - 565 Title/Abstract Full Text View citing articles Show Details
11
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Rx-ID: 29523870 Find similar reactions
Stage #1: With sodium hydroxide in methanol; water
T=20°C; 2 h; Stage #2: T=20°C; 2 h;
Laars, Marju; Raska, Henri; Lopp, Margus; Kanger, Tonis
Tetrahedron Asymmetry, 2010 , vol. 21, # 5 p. 562 - 565 Title/Abstract Full Text View citing articles Show Details
A
B
C
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A
B
C
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12
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Rx-ID: 6925217 Find similar reactions
McCord et al.
Journal of the American Chemical Society, 1957 , vol. 79, p. 5693,5696 Full Text View citing articles Show Details
13
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Rx-ID: 6925218 Find similar reactions
McCord et al.
Journal of the American Chemical Society, 1957 , vol. 79, p. 5693,5696 Full Text View citing articles Show Details
14
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With hydrogenchloride; water
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Rx-ID: 44373753 Find similar reactions
Tereshchenko, Alexander D.; Myronchuk, Julia S.; Leitchenko, Lena D.; Knysh, Irina V.; Tokmakova, Ganna O.; Litsis, Olena O.; Tolmachev, Andrey;
Liubchak, Konstantin; Mykhailiuk, Pavel
Tetrahedron, 2017 , vol. 73, # 6 p. 750 - 757 Title/Abstract Full Text View citing articles Show Details
10 h; Reflux; Hide Experimental Procedure
4.1.3. Morpholine-3-carboxylic acid hydrochloride (4)
Compound 3 (76 g, 358 mmol) was added in several portions toa stirred concentrated hydrochloric acid (340 mmol), and theresulting mixture was refluxed for 10 h, cooled, and concentratedunder the reduced pressure. The residue was treated with KOH(76 g, 13.6 mol) in water (200 mL), stirred for 10 min, andconcentrated at 70 C. The residue was cooled and diluted with HCl(13.8 g, 13.6 mol), and the resulting mixture was concentratedunder reduced pressure. The crude solids, mixture of the productand ammonium chloride, were extracted with hot ethanol severaltimes. The combined fractions were concentrated under reducedpressure give the title compound 4 (42.8 g, 71percent) as white solid; m.p. 229e230; [Found: C, 35.75; H, 6.12; N, 8.15. C5H10ClNO3 requiresC, 35.83; H, 6.01; N, 8.36percent]; 1H NMR (DMSO-d6, 400 MHz):d 14.90e13.40 (br s, 1H), 10.57e9.00 (br s, 2H), 4.28e4.11 (m, 1H),4.06 (dd, J 12.2, 3.3 Hz, 1H), 3.97e3.55 (m, 3H), 3.21 (d, J 13.0 Hz,1H), 3.04 (t, J 9.0 Hz, 1H); 13C NMR (DMSO-d6, 125 MHz): d 167.6,64.8, 62.9, 54.0, 41.7.
15
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Stage #1: With potassium hydroxide in methanol; water
T=20°C; 2 h; Stage #2: T=20°C; 2 h;
Rx-ID: 29523871 Find similar reactions
Laars, Marju; Raska, Henri; Lopp, Margus; Kanger, Tonis
Tetrahedron Asymmetry, 2010 , vol. 21, # 5 p. 562 - 565 Title/Abstract Full Text View citing articles Show Details
16
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Stage #1: With CsOH in methanol; water
T=20°C; 2 h; Stage #2: T=20°C; 2 h;
Rx-ID: 29523872 Find similar reactions
Laars, Marju; Raska, Henri; Lopp, Margus; Kanger, Tonis
Tetrahedron Asymmetry, 2010 , vol. 21, # 5 p. 562 - 565 Title/Abstract Full Text View citing articles Show Details
A
B
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17
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B: 10 g (22%)
With p-toluenesulfonic acid monohydrate; benzyl alcohol in benzene
Hide Experimental Procedure
Mitsubishi Chemical Industries Limited; Okamoto; Shosuke
Patent: US4073913 A1, 1978 ; Title/Abstract Full Text Show Details
Mitsubishi Chemical Industries Limited; Okamoto; Shosuke
Patent: US4097472 A1, 1978 ; Title/Abstract Full Text Show Details
C.D:(D) (D) Benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate A solution of 20 g (0.112 mole) of 4-methyl-2-piperidinecarboxylic acid hydrochloride, 24 g (0.224 mole) of benzyl alcohol and 25.6 g (0.134 mole) of p-toluenesulfonic acid monohydrate in 100 ml of benzene was refluxed for 5 hours with the continuous removal of water through a Dean-Stark water trap. At the end of this period, the solvent was distilled off, and the residue was washed with ether-n-hexane and recrystallized to give 10 g (22percent) of benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate, M.P. 160°-163° C. The following 2-piperidinecarboxylates not previously reported in the chemical literature were synthesised by the aforementioned procedure. Morpholine-3-carboxylic acid hydrochloride was prepared by the procedure described above, and has a melting point of 200°-2° C. B: 10 g (22%)
With p-toluenesulfonic acid monohydrate; benzyl alcohol in benzene
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Mitsubishi Chemical Industries Limited; Okamoto; Shosuke
Patent: US4101653 A1, 1978 ; Title/Abstract Full Text Show Details
C.D:(D) (D) Benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate A solution of 20 g (0.112 mole) of 4methyl-2-piperidinecarboxylic acid hydrochloride, 24 g (0.224 mole) of benzyl alcohol and 25.6 g (0.134 mole) of p-toluenesulfonic acid monohydrate in 100 ml of benzene was refluxed for 5 hours with the continuous removal of water through a Dean-Stark water trap. At the end of this period, the solvent was distilled off, and the residue was washed with ether-n-hexane and recrystallized to give 10 g (22percent) of benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate, M.P. 160°-163° C. The following 2-piperidinecarboxylates not previously reported in the chemical literature were synthesised by the aforementioned procedure. Morpholine-3-carboxylic acid hydrochloride was prepared by the procedure described above, and has a melting point of 200°-202° C. B: 10 g (22%)
With p-toluenesulfonic acid monohydrate; benzyl alcohol in benzene
Hide Experimental Procedure
Mitsubishi Chemical Industries Limited; Okamoto; Shosuke
Patent: US4093712 A1, 1978 ; Title/Abstract Full Text Show Details
C.D:(D) (D) Benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate: A solution of 20 g (0.112 mole) of 4-methyl-2-piperidinecarboxylic acid hydrochloride, 24 g (0.224 mole) of benzyl alcohol and 25.6 g (0.134 mole) of p-toluenesulfonic acid monohydrate in 100 ml of benzene was refluxed for 5 hours with the continuous removal of water through a Dean-Stark water trap. At the end of this period, the solvent was distilled off, and the residue was washed with ether-n-hexane and recrystallized to give 10 g (22percent) of benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate, M.P. 160°-163° C. The following 2-piperidinecarboxylates not previously reported in the chemical literature were synthesised by the aforementioned procedure. Morpholine-3-carboxylic acid hydrochloride was prepared by the procedure described above, and has a melting point of 200°-202° C.