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

HRID 1460220Notes

Reaction equation

HRID 1460220 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 heated at reflux 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 sodium hydroxide solution. 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, and the salt was recrystallized from ethanol-ether to give 89.33 g (49.7%) of the title compound as a white, crystalline solid, mp 154°-155° C.

Workup

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

Sources & evidence

ORD record
ord-e0bd1e1b47214c86879f4fa3957b6f08
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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