1-Phenylpiperazine → HCID 13537610, compound

HRID 638560Notes

Reaction equation

HRID 638560 reaction equation
Br[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])[CH:4]=1.[CH:16]1[CH:17]=[CH:18][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:20][CH:21]=1>CCOCC.CC(C)=O.CCOCC.C(Cl)Cl>[C:19]1([N:22]2[CH2:27][CH2:26][N:25]([CH2:2][C:3]3[O:7][N:6]=[C:5]([C:8]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)=[O:9])[CH:4]=3)[CH2:24][CH2:23]2)[CH:20]=[CH:21][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 2

HCID 70961-PhenylpiperazineHCID 20252669HCID 20252669, compound

Product 1

HCID 13537610HCID 13537610, compoundYield 102.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 21584533Acetone diethyletherSolvent

Procedure

A solution of 3.5 g of (5-bromomethylisoxazol-3-yl)-phenylmethanone in 100 ml of Et2O was added dropwise to a solution of 8.6 g of phenylpiperazine in 375 ml of 20% acetone/Et2O. The resulting mixture was stirred at room temperature for 72 hours. This mixture was washed with water and brine, and dried over MgSO4. Concentration of the product gave an oil, which was taken up in 500 ml of CH2Cl2 and stirred with 20 g of silica gel overnight. The silica was removed by filtration and washed with 500 ml of CH2Cl2. The combined filtrates were concentrated to give 4.7 g of an oil which solidified on standing. Recrystallization from ethanol yielded 3.1 g (69%) of platelets, m.p. 100°-102° C.

Workup

  1. washThis mixture was washed with water and brine
  2. dry with materialdried over MgSO4
  3. customConcentration of the product gave an oil, which
  4. stirringstirred with 20 g of silica gel overnight
  5. customThe silica was removed by filtration
  6. washwashed with 500 ml of CH2Cl2
  7. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-9a33bd7f6971474695ec3cc355b17aea
Source dataset
uspto-grants-1985_12
Patent number
US04562187

Reaction notes

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