Triethylamine → 4-(Acetylthio)-1-[(E)-4-(trifluoromethoxy)cinnamoyl]-piperidine

HRID 381426노트

반응식

HRID 381426 반응식
Cl.[C:2]([S:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)(=[O:4])[CH3:3].C(N(CC)CC)C.[F:19][C:20]([F:34])([F:33])[O:21][C:22]1[CH:32]=[CH:31][C:25](/[CH:26]=[CH:27]/[C:28](Cl)=[O:29])=[CH:24][CH:23]=1>ClCCl>[C:2]([S:5][CH:6]1[CH2:11][CH2:10][N:9]([C:28](=[O:29])/[CH:27]=[CH:26]/[C:25]2[CH:24]=[CH:23][C:22]([O:21][C:20]([F:33])([F:34])[F:19])=[CH:32][CH:31]=2)[CH2:8][CH2:7]1)(=[O:4])[CH3:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 5709512(E)-3-[4-(trifluoromethoxy)phenyl]prop-2-enoyl chlorideHCID 183632904-(Acetylthio)piperidine hydrochloride

생성물 1

HCID 183632734-(Acetylthio)-1-[(E)-4-(trifluoromethoxy)cinnamoyl]-piperidine수율 95.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

In 17 ml of dichloromethane were suspended 1.28 g (6.53 mmol) of 4-(acetylthio)piperidine hydrochloride, and 2.27 ml (16.3 mmol) of triethylamine were added dropwise to the suspension with stirring under ice-cooling. Then, a solution in which 1.80 g (7.18 mmol) of (E)-4-(trifluoromethoxy)cinnamoyl chloride were dissolved in 6 ml of dichloromethane was added dropwise to the reaction mixture, followed by stirring of the mixture at the same temperature for 1 hour. The reaction mixture was subjected to silica gel column chromatography and eluted with a mixed solvent of hexane-ethyl acetate (2:1 to 1:1) to obtain 2.32 g (yield: 95%) of the desired compound as a slightly yellow solid.

후처리

  1. additionwere added dropwise to the suspension
  2. temperaturecooling
  3. additionwas added dropwise to the reaction mixture
  4. stirringby stirring of the mixture at the same temperature for 1 hour
  5. washeluted with a mixed solvent of hexane-ethyl acetate (2:1 to 1:1)

출처 및 근거

ORD 기록
ord-dd0d8d33777e4922a6180c4a6849328e
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306880B1

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