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

HRID 1601364ノート

反応式

HRID 1601364 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8e4484be044e49e8b8f7c520ec3f4b1c
出典データセット
uspto-grants-1999_11
特許番号
US05977152

反応ノート

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