Benzyl chloroformate → Hydrochloric Acid

HRID 1975368Notes

Reaction equation

HRID 1975368 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[CH:30]=[CH:29][C:11]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:16][CH2:15]2)=[O:13])=[CH:10][CH:9]=1)([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:37]([O:44][C:45]([Cl:47])=[O:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1(C)C=CC=CC=1>[ClH:28].[ClH:47].[CH:1]([O:4][CH2:5][CH2:6][N:7]([C:45]([O:44][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:46])[C:8]1[CH:30]=[CH:29][C:11]([C:12]([N:14]2[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:18][CH2:19]2)=[O:13])=[CH:10][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 98455471-[4-(2-Isopropyloxyethyl)aminobenzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine

Product 2

HCID 313Hydrochloric AcidHCID 67825198HCID 67825198, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1.2 g of 1-{4-[N-(2-isopropyloxyethyl)amino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine are dissolved in 15 ml of toluene, and 1.1 g of potash are added. The mixture is stirred for 10 minutes at RT and then 1.9 g of chloroformic acid benzyl ester in 4 ml of toluene are added dropwise thereto. The mixture is stirred overnight at RT and concentrated by evaporation, the residue is partitioned between dichloromethane and water, and the mixture is concentrated by evaporation and chromatographed over silica gel (eluant: dichloromethane/acetone 9:1). Treatment with alcoholic hydrochloric acid yields 1-{4-[N-(2-isopropyloxyethyl)benzyloxycarbonylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride having a melting point of 135°-137°.

Workup

  1. stirringThe mixture is stirred overnight at RT
  2. concentrationconcentrated by evaporation
  3. customthe residue is partitioned between dichloromethane and water
  4. concentrationthe mixture is concentrated by evaporation
  5. customchromatographed over silica gel (eluant: dichloromethane/acetone 9:1)

Sources & evidence

ORD record
ord-c08d58e84c844f278ca980b84fb1af8d
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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