Benzyl Chloride → 1-(Phenylmethyl)-4-piperidinecarboxylic acid ethyl ester hydrochloride

HRID 476923Notes

Reaction equation

HRID 476923 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.[CH2:12]([Cl:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[ClH:19].[CH2:8]([O:7][C:5]([CH:4]1[CH2:3][CH2:2][N:1]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10]1)=[O:6])[CH3:9]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 10340Sodium CarbonateHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 700922841-(Phenylmethyl)-4-piperidinecarboxylic acid ethyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 100 g (0.637 mole) of ethyl isonipecotate, 80.64 g (0.64 mole) of benzyl chloride and 67.84 g (0.64 mole) of sodium carbonate in 1 liter of absolute ethanol was refluxed for 8 hours and then was stirred at room temperature for 10 hours. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride phase was dried over magnesium sulfate, and the solvent was removed in vacuo to give the free base of the title compound as a liquid. The free base was converted to the hydrochloride salt, and the salt was recrystallized from ethanol-ether to give 89.33 g (49.7%) of white, crystalline solid, m.p. 154°-155° C.

Workup

  1. temperaturewas refluxed for 8 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between methylene chloride and dilute sodium hydroxide
  4. dry with materialThe methylene chloride phase was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1e7565d87f794d9bbb227050681b4aa6
Source dataset
uspto-grants-1989_12
Patent number
US04886794

Reaction notes

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