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

HRID 1737195Notes

Reaction equation

HRID 1737195 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3759315af56c4fc59f0c8765ed19fff2
Source dataset
uspto-grants-1999_10
Patent number
US05962440

Reaction notes

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