Benzyl Bromide → Ethyl 1-benzylpiperidine-3-carboxylate

HRID 432816ノート

反応式

HRID 432816 の反応式
[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

参加物

4

反応物 2

HCID 7498Benzyl BromideHCID 98969Ethyl nipecotate

生成物 1

HCID 2736370Ethyl 1-benzylpiperidine-3-carboxylate収率 78.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-83ed16de13cb428d92e81f5610e6e879
出典データセット
uspto-grants-2003_12
特許番号
US06664271B1

反応ノート

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