Benzyl Bromide → Ethyl 1-benzylpiperidine-3-carboxylate

HRID 432816노트

반응식

HRID 432816 반응식
[NH:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[CH2:12]([N:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

4

반응물 2

HCID 7498Benzyl BromideHCID 98969Ethyl nipecotate

생성물 1

HCID 2736370Ethyl 1-benzylpiperidine-3-carboxylate수율 78.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Commercially available ethyl nipecotate (509.7 mg; 3.25 mmol) was dissolved in dichloromethane (12 ml). Dilsopropylethylamine (570 μl; 3.27 mmol) was added, followed by commercially available benzyl bromide (386 μl; 3.25 mmol) and the mixture stirred at ambient temperature for approximately 20 hours. The mixture was then evaporated at ambient temperature under reduced pressure. The crude product was purified by chromatography on silica eluting with 80% ethyl acetate in hexane, giving ethyl 1-benzyl-3-piperidinecarboxylate (634.4 mg) as a colorless oil. MS m/z (positive ion) 248 (MH+; 100).

후처리

  1. additionDilsopropylethylamine (570 μl; 3.27 mmol) was added
  2. customThe mixture was then evaporated at ambient temperature under reduced pressure
  3. customThe crude product was purified by chromatography on silica eluting with 80% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-83ed16de13cb428d92e81f5610e6e879
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664271B1

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