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

HRID 1413728Notes

Reaction equation

HRID 1413728 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-a6c403d27a8246ca8eb268df86061e36
Source dataset
uspto-grants-1981_02
Patent number
US04251438

Reaction notes

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