Benzyl Bromide → ethyl 1-benzylpiperidine-3-carboxylate

HRID 432816Notes

Reaction equation

HRID 432816 reaction equation
[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

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 98969Ethyl nipecotate

Product 1

HCID 2736370ethyl 1-benzylpiperidine-3-carboxylateYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-83ed16de13cb428d92e81f5610e6e879
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Reaction notes

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