Water → 1-Acetyl-4-(3-hydroxyphenyl)piperazine

HRID 27728Notes

Reaction equation

Br.Br.[N:3]1([C:9]2[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.O.C(=O)([O-])O.[Na+].[C:22](OC(=O)C)(=[O:24])[CH3:23]>ClC(Cl)Cl>[C:22]([N:6]1[CH2:5][CH2:4][N:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[CH2:8][CH2:7]1)(=[O:24])[CH3:23]

Participants

Conditions

Temperature: 10 °C

Procedure

To a stirred solution of 80 parts of 3-(1-piperazinyl)phenol dihydrobromide in 360 parts of water and 180 parts of trichloromethane are added portionwise 42 parts of sodium hydrogen carbonate at 10° C. Then there are added dropwise, during a 15 minutes-period, 26 parts of acetic acid anhydride while cooling at 10° C. Upon completion, stirring is continued for 3 hours at room temperature. The precipitated product is filtered off, washed with water and crystallized from 2-propanol, yielding 37 parts (70%) of 1-acetyl-4-(3-hydroxyphenyl)piperazine; mp. 186.1° C.

Workup

filtrationThe precipitated product is filtered off
washwashed with water
customcrystallized from 2-propanol

Sources & evidence

ORD record: ord-9e7a05195d784d57b5836081ab25c218
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04223036

Reaction notes

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