Potassium Iodide → N-(4-(1-(4-(4-fluorophenyl)piperazin-1-yl)-1-methylethyl)phenylmethyl)acetamide dihydrochloride monohydrate

HRID 1282124Notes

Reaction equation

[NH2:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C:13](=[O:15])[CH3:14])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[Cl:16][CH2:17][CH2:18][N:19]([CH2:27][CH2:28]Cl)[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CS(C)=O.O>[OH2:15].[ClH:16].[ClH:16].[F:26][C:23]1[CH:24]=[CH:25][C:20]([N:19]2[CH2:27][CH2:28][N:1]([C:2]([C:5]3[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C:13](=[O:15])[CH3:14])=[CH:7][CH:6]=3)([CH3:3])[CH3:4])[CH2:17][CH2:18]2)=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N-(4-(1-amino-1-methylethyl)phenylmethyl)-acetamide (1.55 g) and N,N-di(2-chloroethyl)-4-fluoroaniline (1.5 g) in dimethyl sulfoxide (30 ml) were added potassium carbonate (3.12 g) and potassium iodide (2.50 g) and the mixture was stirred at 80° C. for 24 hr. The reaction mixture was poured into water (300 ml) and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel chromatography (developing solvent; ethyl acetate:hexane=3:1) and treated with 1M hydrochloric acid-ether in ethanol to give the title compound (0.33 g) as white crystals.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated
customthe obtained residue was purified by silica gel chromatography (developing solvent; ethyl acetate:hexane=3:1)
additiontreated with 1M hydrochloric acid-ether in ethanol

Sources & evidence

ORD record: ord-e5489caa0e9b47868fbcc60aa2f95bca
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455528B1

Reaction notes

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