Hydrochloric Acid → HCID 20087980, compound

HRID 275370Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[CH:15]=3)[N:10]([CH:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][N:26]4[CH2:30][CH2:29][N:28]([CH:31]([CH3:33])[CH3:32])[C:27]4=[O:34])[CH2:20][CH2:19]3)[CH:9]=2)=[CH:4][CH:3]=1.CS(C)=O.[ClH:39]>O>[Cl:39][C:9]1[N:10]([CH:18]2[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][N:26]3[CH2:30][CH2:29][N:28]([CH:31]([CH3:32])[CH3:33])[C:27]3=[O:34])[CH2:22][CH2:23]2)[C:11]2[C:16]([C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-(4-Fluorophenyl)-5-methyl-1-[1-[2-[3-(2-propyl)imidazolidin-2-on-1yl]ethyl]-4-piperidyl)-1H-indole 4h (3.0 g), dimethylsulphoxide (0.51 g) and conc. aqueous HCl (1 ml) was heated to 60° C. for 0.5 h under stirring. The reaction mixture was cooled to room temperature and water was added. The solution was extracted with ethyl acetate (2×50 ml). The combined organic phases were washed with 4N aqueous NaOH and brine. Evaporation of the solvent gave an oil which was purified by column chromatography on silica gel (eluted with ethyl acetate/heptane 1:3). This afforded the title compound which crystallized from diethyl ether. Yield 0.4 g, mp 127°-130° C.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionThe solution was extracted with ethyl acetate (2×50 ml)
washThe combined organic phases were washed with 4N aqueous NaOH and brine
customEvaporation of the solvent
customgave an oil which
customwas purified by column chromatography on silica gel (eluted with ethyl acetate/heptane 1:3)

Sources & evidence

ORD record: ord-6f2b9343f8ca4c88ba5b87c3007ddbc0
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05393761

Reaction notes

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