Chloroacetyl chloride → N-(1-Benzyl-piperidin-4-yl)-2-chloro-N-isopropyl-acetamide

HRID 1662115노트

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HRID 1662115 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15]([CH3:17])[CH3:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl:27][CH2:28][C:29](Cl)=[O:30]>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:15]([CH3:17])[CH3:16])[C:29](=[O:30])[CH2:28][Cl:27])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 107283101-Benzyl-N-isopropylpiperidin-4-amine

생성물 1

HCID 66565165N-(1-Benzyl-piperidin-4-yl)-2-chloro-N-isopropyl-acetamide수율 50.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a mixture of 1-benzyl-4-(isopropylamino)piperidine (8 g, 34.45 mmol) and DIPEA (7.2 mL, 41.3 mmol) in 200 mL of dichloromethane was added dropwise a solution of 2-chloroacetyl chloride (3.01 mL, 37.9 mmol) in dichloromethane (400 mL) at 0° C. The reaction mixture was stirred at 0° C. for 15 min and then at room temperature for 2 h. The reaction mixture was then washed with saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by flash column chromatography (ethyl acetate/hexane/triethylamine: 42.5/56.5/1) to give 5.35 g of the title intermediate as a viscous oil (50% yield).

후처리

  1. waitat room temperature for 2 h
  2. washThe reaction mixture was then washed with saturated sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by flash column chromatography (ethyl acetate/hexane/triethylamine: 42.5/56.5/1)

출처 및 근거

ORD 기록
ord-8ad26682b0504b708107dd6c8d9b3147
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030502B2

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