Dibenzosuberenol → 4-[4-(4-fluorophenyl)-1-piperazinyl]butyrylamino-5H-dibenzo[a,d]cycloheptene

HRID 579754Notes

Reaction equation

[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6](O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][CH2:32][C:33]([NH2:35])=[O:34])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1>C(O)(=O)C>[F:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][CH2:32][C:33]([NH:35][C:1]3[C:11]4[CH:10]=[CH:9][C:8]5[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=5[CH2:6][C:5]=4[CH:4]=[CH:3][CH:2]=3)=[O:34])[CH2:26][CH2:25]2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 200 mg of 5H-dibenzo[a,d]cyclohepten-5-ol, 300 mg of 4-[4-(4-fluorophenyl)-1-piperazinyl]butyramide and 8 ml of acetic acid is stirred at 70° C. for 20 hours. The acetic acid is distilled off under reduced pressure and 100 ml of chloroform is added to the residue. The solution is washed successively with 10% aqueous potassium carbonate solution, water and saturated aqueous sodium chloride solution, and dried over magnesium sulfate, and the chrloroform is distilled off. The residue is chromatographed on silica gel with chloroform-methanol (100:3) to give 250 mg of the title compound. m.p. 233°-235° C. (recrystallized from chloroform-n-hexane);

Workup

distillationThe acetic acid is distilled off under reduced pressure and 100 ml of chloroform
additionis added to the residue
washThe solution is washed successively with 10% aqueous potassium carbonate solution, water and saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
distillationthe chrloroform is distilled off
customThe residue is chromatographed on silica gel with chloroform-methanol (100:3)

Sources & evidence

ORD record: ord-d8fa09e96f8d40c594cab58949f5cceb
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04749703

Reaction notes

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