Water → HCID 19372964, compound

HRID 128933Notes

Reaction equation

[C:1]([NH:4][CH2:5][C:6]1[S:7][C:8]([C:11](=[O:16])[CH2:12][CH2:13][CH2:14]Cl)=[CH:9][CH:10]=1)(=[O:3])[CH3:2].Br.[F:18][C:19]([F:33])([F:32])[C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1.[C:34](=[O:37])([O-:36])[O-].[K+].[K+].[I-].[K+].[OH2:42]>C1(C)C=CC=CC=1.CN(C)C=O>[C:11]([OH:16])(=[O:42])/[CH:12]=[CH:13]/[C:34]([OH:36])=[O:37].[C:1]([NH:4][CH2:5][C:6]1[S:7][C:8]([C:11](=[O:16])[CH2:12][CH2:13][CH2:14][N:29]2[CH2:28][CH2:27][N:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([C:19]([F:32])([F:33])[F:18])[CH:21]=3)[CH2:31][CH2:30]2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-acetylaminomethyl-5-(4-chlorobutyryl)thiophene (3 g), 1-(3-trifluoromethylphenyl)piperazine hydrobromide (4 g), potassium carbonate (3.5 g), potassium iodide (2 g), dimethylformamide (25 ml), and toluene (25 ml) was stirred at 60° C. for 7 hours. The reaction mixture was poured into water, extracted with toluene, and dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and converted to fumarate, followed by recrystallization from acetone to give 0.9 g of 1-(4-(5-acetylaminomethyl -2-thienyl)-4-oxobutyl)-4-(3-trifluoromethylphenyl)piperazine fumarate as white crystals, m.p. 135°-137° C.

Workup

extractionextracted with toluene
dry with materialdried over magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography
customfollowed by recrystallization from acetone

Sources & evidence

ORD record: ord-a24f0d1bc66a42e6aef6dd7024c4ac94
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05466691

Reaction notes

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