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

HRID 1737195ノート

反応式

HRID 1737195 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3759315af56c4fc59f0c8765ed19fff2
出典データセット
uspto-grants-1999_10
特許番号
US05962440

反応ノート

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