Benzyl Alcohol → Benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate

HRID 839861Notes

Reaction equation

HRID 839861 reaction equation
Cl.[CH3:2][CH:3]1[CH2:8][CH2:7][NH:6][CH:5]([C:9]([OH:11])=[O:10])[CH2:4]1.[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([OH:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1.O>C1C=CC=CC=1>[C:21]1([CH3:31])[CH:22]=[CH:23][C:24]([S:27]([OH:30])(=[O:28])=[O:29])=[CH:25][CH:26]=1.[CH3:2][CH:3]1[CH2:8][CH2:7][NH:6][CH:5]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:4]1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962Water2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 219885124-Methylpiperidine-2-carboxylic acid hydrochloride

Product 1

HCID 22754709Benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonateYield 22%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 20 g (0.112 mole) of 4-methyl-2-piperidinecarboxylic acid hydrochloride, 24 g (0.224 mole) of benzyl alcohol and 25.6 g (0.134 mole) of p-toluenesulfonic acid monohydrate in 100 ml of benzene was refluxed for 5 hours with the continuous removal of water through a Dean-Stark water trap. At the end of this period, the solvent was distilled off, and the residue was washed with ether-n-hexane and recrystallized to give 10 g (22%) of benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate, M.P. 160°-163° C. The following 2-piperidinecarboxylates not previously reported in the chemical literature were synthesized by the aforementioned procedure.

Workup

  1. distillationAt the end of this period, the solvent was distilled off
  2. washthe residue was washed with ether-n-hexane
  3. customrecrystallized

Sources & evidence

ORD record
ord-888b294fd003457aad2a89b9c79a05fa
Source dataset
uspto-grants-1978_06
Patent number
US04097472

Reaction notes

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