Benzyl Chloride → Ethyl 1-benzylpiperidine-4-carboxylate

HRID 1743739Notes

Reaction equation

HRID 1743739 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(OCC)(=O)C.O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 90423Ethyl 1-benzylpiperidine-4-carboxylateYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 22728543Water ethylacetateSolvent

Procedure

1 g (6.4 mmol) of piperidine-4-carboxylic acid ethyl ester is mixed in 10 ml of absolute ethanol with 0.75 ml (6.4 mmol) of benzyl chloride and 1.52 g (11 mmol) of potassium carbonate. The batch is stirred for 30 hours at room temperature. It is then dispersed in ethyl acetate/water. The combined organic phase is washed with water, dried, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with hexane:ethyl acetate=1:1 as an eluant. 991 mg (64% of theory) of N-benzylpiperidine-4-carboxylic acid ethyl ester is obtained.

Workup

  1. washThe combined organic phase is washed with water
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with hexane

Sources & evidence

ORD record
ord-d45bc13e63594a2083563c16eee988cd
Source dataset
uspto-grants-2006_03
Patent number
US07012081B2

Reaction notes

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