Benzyl Chloride → ethyl 1-benzylpiperidine-3-carboxylate

HRID 1269742Notes

Reaction equation

HRID 1269742 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16]1>CN(C)C=O>[CH2:1]([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 98969Ethyl nipecotate

Product 1

HCID 2736370ethyl 1-benzylpiperidine-3-carboxylateYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Benzyl chloride (5.5 ml, 47.8 mmol) and potassium carbonate (8.3 g, 60.1 mmol) were added to a solution of ethyl 3-piperidinecarboxylate (6.55 g, 40.0 mmol) in N,N-dimethylformamide (20 ml), and the resulting mixture was stirred at 100° C. for 10 hours. After completion of the reaction, the reaction solution was filtered and the filtrate was subjected to azeotropic concentration with toluene. The resulting residue was purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1) to obtain ethyl 1-benzyl-3-piperidinecarboxylate (7.45 g, 75.3%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction solution was filtered
  3. concentrationthe filtrate was subjected to azeotropic concentration with toluene
  4. customThe resulting residue was purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-33d2e0ea00904390b3802fbffdd2d928
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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