Chloroform → trans-N-[3-methoxy-1-(phenylmethyl)-4-piperidinyl]-3-(trifluoromethyl)benzamide

HRID 981301노트

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HRID 981301 반응식
[CH3:1][O:2][C@H:3]1[C@H:8]([NH2:9])[CH2:7][CH2:6][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4]1.ClC(Cl)Cl.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27]>C(N(CC)CC)C>[CH3:1][O:2][C@H:3]1[C@H:8]([NH:9][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([C:22]([F:21])([F:32])[F:33])[CH:24]=2)[CH2:7][CH2:6][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4]1

참가 물질

5

반응물 3

HCID 6212ChloroformHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 13677827trans-3-Methoxy-1-(phenylmethyl)-4-piperidinamine

생성물 1

HCID 67928762trans-N-[3-methoxy-1-(phenylmethyl)-4-piperidinyl]-3-(trifluoromethyl)benzamide수율 80.9%

시약·촉매·용매 1

HCID 8471Triethylamine용매2회

실험 절차

To a stirred solution of 10 parts of trans-3-methoxy-1-(phenylmethyl)-4-piperidinamine and 5.95 parts of N,N-diethylethanamine in 75 parts of trichloromethane was added dropwise a solution of 10.4 parts of 3-(trifluoromethyl)benzoyl chloride in 15 parts of N,N-diethylethanamine while cooling in an ice bath. Upon completion, stirring was continued for 20 hours at room temperature. The mixture was washed twice with a sodium hydroxide solution 5% and once with water and then dried, filtered and evaporated in vacuo. After crystallization of the residue from 27 parts of methylbenzene, the product was filtered off, washed with 45 parts of methylbenzene and dried, yielding 14.4 parts (80.9%) of trans-N-[3-methoxy-1-(phenylmethyl)-4-piperidinyl]-3-(trifluoromethyl)benzamide; mp. 135.2° C. (interm. 8).

후처리

  1. temperaturewhile cooling in an ice bath
  2. washThe mixture was washed twice with a sodium hydroxide solution 5% and once with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customAfter crystallization of the residue from 27 parts of methylbenzene
  7. filtrationthe product was filtered off
  8. washwashed with 45 parts of methylbenzene
  9. customdried

출처 및 근거

ORD 기록
ord-2b7d0ae2b55344c7957c12646d94faaf
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04990521

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