Benzyl chloroformate → 1-Piperidinecarboxylic acid, 4-isothiocyanato-, phenylmethyl ester

HRID 1856550Notes

Reaction equation

HRID 1856550 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][N:7](CC2C=CC=CC=2)[CH2:6][CH2:5]1)=[C:2]=[S:3].[C:17](Cl)(=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC1C=CC=CC=1>[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:26])[CH2:6][CH2:5]1)=[C:2]=[S:3]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 118065461-benzyl-4-isothiocyanatopiperidine

Product 1

HCID 543052121-Piperidinecarboxylic acid, 4-isothiocyanato-, phenylmethyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 28.4 parts of 4-isothiocyanato-1-(phenylmethyl)piperidine in 315 parts of methylbenzene are added dropwise 41 parts of (phenylmethyl) carbonochloridate at room temperature. Upon completion, the whole is heated to reflux and stirring is continued overnight at reflux temperature. The reaction mixture is cooled and the solvent is evaporated. The residue is purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated, yielding 32 parts (97%) of (phenylmethyl) 4-isothiocyanato-1-piperidinecarboxylate as a residue.

Workup

  1. temperatureUpon completion, the whole is heated
  2. temperatureto reflux
  3. temperatureat reflux temperature
  4. temperatureThe reaction mixture is cooled
  5. customthe solvent is evaporated
  6. customThe residue is purified by column-chromatography over silica gel
  7. customThe pure fractions are collected
  8. customthe eluent is evaporated

Sources & evidence

ORD record
ord-7c3a7183c7274f93a55140b54c2686d8
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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