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

HRID 66317Notes

Reaction equation

HRID 66317 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.

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-42bc25758a7f4cac9db4941d0524cddf
Source dataset
uspto-grants-1978_12
Patent number
US04131673

Reaction notes

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