Benzyl Bromide → 1-Benzylpiperidine-2-carboxylic acid--hydrogen chloride (1/1)

HRID 1737195노트

반응식

HRID 1737195 반응식
[ClH:1].[NH:2]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:3]1[C:4]([O:6]CC)=[O:5].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:1].[CH2:13]([N:2]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:3]1[C:4]([OH:6])=[O:5])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 12436225Ethyl piperidine-2-carboxylate--hydrogen chloride (1/1)

생성물 1

HCID 130902421-Benzylpiperidine-2-carboxylic acid--hydrogen chloride (1/1)수율 96%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of ethyl pipecolinate hydrochloride (10 g, 52 mmol), benzylbromide (7 mL, 57 mmol) and potassium carbonate (15 g, 114 mmol) in DMF (80 mL) was stirred at room temperature overnight. The solvent was removed in vacuo. The residue was partitioned between dichloromethane (100 mL) and water (50 mL). The aqueous layer was extracted with dichloromethane (2×100 mL), dried over Na2SO4, then evaporated to give a yellow oil. The crude product was chromatographed (500 g silica gel) eluting with a stepgradient of 8%-15% ethyl acetate in hexane. Pure fractions were combined to give title compound (12.3 g, 96%) as a colorless oil.

후처리

  1. customThe solvent was removed in vacuo
  2. customThe residue was partitioned between dichloromethane (100 mL) and water (50 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (2×100 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customto give a yellow oil
  7. customThe crude product was chromatographed (500 g silica gel)
  8. washeluting with a stepgradient of 8%-15% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-3759315af56c4fc59f0c8765ed19fff2
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962440

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