Water → (2R)-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-propargylpiperazine

HRID 584193ノート

反応式

HRID 584193 の反応式
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=1)=[O:7].C(=O)([O-])[O-].[K+].[K+].[CH2:38](Br)[C:39]#[CH:40].O>CN(C)C=O>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:40][C:39]#[CH:38])[CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=1)=[O:7]

参加物

6

反応物 4

HCID 962WaterHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 54478438(2R)-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine

生成物 1

HCID 53973560(2R)-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-propargylpiperazine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred mixture of (2R)-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine (943 mg) and potassium carbonate (880 mg) in dimethylformamide (10 ml) was added propargyl bromide (0.2 ml) at room temperature. After 1 hour, the reaction mixture was poured into water (100 ml) and extracted with ethyl acetate. The extract was washed with brine and concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel using a mixture of hexane and ethyl acetate (5:1) as eluent to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-propargylpiperazine (1.09 g) as an oil.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by column chromatography on silica gel using
  5. additiona mixture of hexane and ethyl acetate (5:1) as eluent

出典と根拠

ORDレコード
ord-23ac934a451d4affb3fd389c94a9c9e6
出典データセット
uspto-grants-2005_08
特許番号
US06924278B2

反応ノート

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