Hydrochloric Acid → HCID 70382542, compound

HRID 232334Notes

Reaction equation

[CH2:1]([N:3]([CH2:16][CH3:17])[CH2:4][CH2:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][C:11](F)=[CH:10][CH:9]=1)[CH3:2].[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.C(=O)([O-])[O-].[K+].[K+].[ClH:29]>CO.O.CS(C)=O>[OH2:15].[ClH:29].[ClH:29].[CH2:1]([N:3]([CH2:16][CH3:17])[CH2:4][CH2:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)=[CH:10][CH:9]=1)[CH3:2]

Participants

Conditions

Temperature: 165 °C

Procedure

A mixture of 50.0 g (0.211 mol) 4-(diethylamino)-1-(4-fluorophenyl)butanone, 29.0 g (0.42 mol) imidazole, 58.24 g (0.42 mol) anhydrous potassium carbonate and 50 mL dimethylsulfoxide is heated to 150° C. for 18 hr and to 165° C. for 3 hr. After this time, the mixture is treated with 500 mL H2O and is extracted with 2×400 mL methylene chloride. The organic layers are washed with 5×300 mL water. The organic layer is dried over sodium sulfate, filtered and the solvent evaporated to provide crude title compound as free base. This material is dissolved in 200 mL methanol, acidified to pH=1 with hydrochloric acid (gas) and the solvent removed in vacuo. The residue is recrystallized from methanol-isopropanol (2/3) to provide the title compound.

Workup

extractionis extracted with 2×400 mL methylene chloride
washThe organic layers are washed with 5×300 mL water
dry with materialThe organic layer is dried over sodium sulfate
filtrationfiltered
customthe solvent evaporated
customto provide crude title compound as free base
customthe solvent removed in vacuo
customThe residue is recrystallized from methanol-isopropanol (2/3)

Sources & evidence

ORD record: ord-2175de29a7bc4284beb6516e8ad26f67
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04851526

Reaction notes

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