Benzyl chloroformate → Benzyl-3-oxo-2-(phenylmethyl)-1-piperazinecarboxylate

HRID 1981621Notes

Reaction equation

HRID 1981621 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[C:12]1([CH2:18][CH:19]2[NH:24][CH2:23][CH2:22][NH:21][C:20]2=[O:25])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:5]([O:4][C:2]([N:24]1[CH2:23][CH2:22][NH:21][C:20](=[O:25])[CH:19]1[CH2:18][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 135204163-Benzylpiperazin-2-one

Product 1

HCID 13520417Benzyl-3-oxo-2-(phenylmethyl)-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Benzyl chloroformate (8.5 g.) is added to a stirred mixture of 3-(phenylmethyl)piperazinone (XXIX, Example 62, 6.8 g.), chloroform (75 ml.), and saturated sodium bicarbonate solution (20 ml.). After 30 minutes the chloroform phase is separated, washed twice with water, and concentrated. The residual oil is crystallized from ethyl acetate-SSB and then ethyl acetate again to give the title compound, m.p. 125°-127.5°.

Workup

  1. customAfter 30 minutes the chloroform phase is separated
  2. washwashed twice with water
  3. concentrationconcentrated
  4. customThe residual oil is crystallized from ethyl acetate-SSB

Sources & evidence

ORD record
ord-bab77e3fc28749f1903d16ef98f79847
Source dataset
uspto-grants-1986_06
Patent number
US04593098

Reaction notes

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