Triethylamine → cis-1-[4-[3-Methoxy-4-[(phenylmethyl)amino]-1-piperidinyl]-1-oxobutyl]pyrrolidine

HRID 1110388노트

반응식

HRID 1110388 반응식
Cl[CH2:2][CH2:3][CH2:4][C:5]([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6].[CH3:12][O:13][C@H:14]1[C@@H:19]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][CH2:17][NH:16][CH2:15]1.C(N(CC)CC)C>CN(C)C=O>[CH3:12][O:13][C@H:14]1[C@@H:19]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][CH2:17][N:16]([CH2:2][CH2:3][CH2:4][C:5]([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[O:6])[CH2:15]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 3040794-Chloro-1-(pyrrolidin-1-yl)butan-1-one2회HCID 13677805cis-3-methoxy-N-(phenylmethyl)-4-piperidinamine

생성물 1

HCID 70048899cis-1-[4-[3-Methoxy-4-[(phenylmethyl)amino]-1-piperidinyl]-1-oxobutyl]pyrrolidine수율 59%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

A mixture of 43.9 parts of 1-(4-chloro-1-oxobutyl)pyrrolidine, 55.1 parts of cis-3-methoxy-N-(phenylmethyl)-4-piperidinamine, 37.8 parts of N,N-diethylethanamine and 900 parts of N,N-dimethylformamide was stirred overnight at 70° C. Another portion of 4.4 parts of 1-(4-chloro-1-oxobutyl)pyrrolidine was added and stirring was continued overnight at 70° C. The reaction mixture was evaporated and the residue was taken up in a mixture of water and sodium carbonate. The product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 53.1 parts (59.0%) of cis-1-[4-[3-methoxy-4-[(phenylmethyl)amino]-1 piperidinyl]-1-oxobutyl]pyrrolidine as a residue (int. 42).

후처리

  1. stirringstirring
  2. waitwas continued overnight at 70° C
  3. customThe reaction mixture was evaporated
  4. additionthe residue was taken up in a mixture of water and sodium carbonate
  5. extractionThe product was extracted with dichloromethane
  6. washThe extract was washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated

출처 및 근거

ORD 기록
ord-6921b604a46148ffbd6787e78126adb2
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04975439

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