1-Phenylpiperazine → 1-[2-(4-Phenylbutyl)phenoxy]-3-(4-phenylpiperazin-1-yl)-2-propanol

HRID 743204Notes

Reaction equation

[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]1([CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:33]=[CH:32][CH:31]=[CH:30][C:24]=2[O:25][CH2:26][CH:27]2[CH2:29][O:28]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[C:13]1([CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:33]=[CH:32][CH:31]=[CH:30][C:24]=2[O:25][CH2:26][CH:27]([OH:28])[CH2:29][N:10]2[CH2:11][CH2:12][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 50 °C

Procedure

3.89 g of N-phenylpiperazine were added to a solution of 1.69 g of 2-[2-(4-phenylbutyl)phenoxymethyl]oxirane [prepared as described in Example 1(a)] in 30 ml of acetonitrile, and the resulting mixture was stirred at 50° C. for 3 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 2:3 by volume mixture of ethyl acetate and hexane as the eluent, to give 920 mg (yield 34%) of the title compound as a colorless oil.

Workup

customAt the end of this time, the solvent was removed by distillation under reduced pressure
customthe resulting residue was purified by column chromatography through silica gel
additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record: ord-3c28caa52bb344538d1fbb99ad9bfd21
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556864

Reaction notes

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