Acetyl chloride → (+/-)-1-BOC-4-acetyl-3-phenyl-piperazine

HRID 530626ノート

反応式

HRID 530626 の反応式
[C:1]1([CH:7]2[NH:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:27](Cl)(=[O:29])[CH3:28]>ClCCl.C(=O)(O)[O-].[Na+]>[C:16]([O:15][C:13]([N:9]1[CH2:10][CH2:11][N:12]([C:27](=[O:29])[CH3:28])[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

参加物

6

反応物 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 2735358Tert-butyl 3-phenylpiperazine-1-carboxylate

生成物 1

HCID 67083964(+/-)-1-BOC-4-acetyl-3-phenyl-piperazine収率 54%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 516892Sodium Bicarbonate溶媒

実験手順

To a mixture of tert-butyl 3-phenylpiperazine-1-carboxylate (400 mg, 1.52 mmol) and triethyl amine (309 mg, 3.05 mmol) in dichloromethane (5 mL) was added acetyl chloride (156 mg, 1.98 mmol) at 0° C. After stirring for 3 h at room temperature, the reaction mixture was diluted with saturated sodium bicarbonate solution and dichloromethane. The aqueous part was extracted with dichloromethane and the combined organic part was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (20/1 dichloromethane/methanol) to afford 4-acetyl-3-phenyl-piperazine-1-carboxylic acid tert-butyl ester (250 mg, 54%). [M-BOC]H+=205.

後処理

  1. extractionThe aqueous part was extracted with dichloromethane
  2. dry with materialthe combined organic part was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (20/1 dichloromethane/methanol)

出典と根拠

ORDレコード
ord-5490e463d5c44e0786f3c839e3fc72c5
出典データセット
uspto-grants-2016_05
特許番号
US09353096B2

反応ノート

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