1-Phenylpiperazine → 1-Piperazinecarboxylic acid, 4-phenyl-, phenylmethyl ester

HRID 1090113Notes

Reaction equation

HRID 1090113 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([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.C1C=CC=CC=1.C(N(CC)CC)C.CCCCCC>[C:2]([N:21]1[CH2:22][CH2:23][N:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:19][CH2:20]1)([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3]

Participants

7

Reactant 2

HCID 70961-PhenylpiperazineHCID 10387Benzyl chloroformate

Product 1

HCID 98792541-Piperazinecarboxylic acid, 4-phenyl-, phenylmethyl ester

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 4.4 g of benzyl chloroformate in toluene is added to a solution comprising 4.05 g of N-phenylpiperazine in 50 cm3 of benzene and 2.5 g of triethylamine, at a temperature between +5° C. and +10° C. The whole is allowed to return to ambient temperature and agitated for 2 hours. The triethylamine chloride is filtered off and evaporated to dryness. An oily residue is obtained which is solidified in n-hexane and 7.1 g of expected product is recovered. m.p.=49°-51° C. After recrystallization from an ethyl ether -n-hexane mixture, m.p.=51°-52° C.

Workup

  1. customat a temperature between +5° C. and +10° C
  2. customto return to ambient temperature
  3. filtrationThe triethylamine chloride is filtered off
  4. customevaporated to dryness
  5. customAn oily residue is obtained which
  6. custom7.1 g of expected product is recovered
  7. customAfter recrystallization from an ethyl ether -n-hexane mixture, m.p.=51°-52° C.

Sources & evidence

ORD record
ord-a43f6a1555a54d77b0f5d6de0928ea06
Source dataset
uspto-grants-1992_01
Patent number
US05081130

Reaction notes

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