Chlorotrimethylsilane → 2-(4-dimethylamino-4-(4-fluorophenyl)cyclohexylidene)-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone hydrochloride

HRID 2357506Notes

Reaction equation

HRID 2357506 reaction equation
[Cl:1][Si](C)(C)C.[CH3:6][N:7]([CH3:38])[C:8]1([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH2:13][CH2:12][C:11](=[CH:14][C:15]([N:17]2[CH2:21][CH2:20][CH:19]([C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)[CH2:18]2)=[O:16])[CH2:10][CH2:9]1>CC(CC)=O>[ClH:1].[CH3:38][N:7]([CH3:6])[C:8]1([C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)[CH2:13][CH2:12][C:11](=[CH:14][C:15]([N:17]2[CH2:21][CH2:20][CH:19]([C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)[CH2:18]2)=[O:16])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 10345144HCID 10345144, compound

Product 1

HCID 103451432-(4-dimethylamino-4-(4-fluorophenyl)cyclohexylidene)-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone hydrochloride

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Chlorotrimethylsilane (0.13 ml, 1.01 mmole) was added to a solution of 2-(4-dimethylamino-4-(4-fluorophenyl)-cyclohexylidene)-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]ethanone (300 mg, 0.67 mmole) in ethyl methyl ketone (25 ml) and stirred for 2 hours at RT. The hydrochloride (300 mg, 93%) thereupon precipitated as a diastereoisomer mixture with a melting point of 189°-194° C. in the form of a colourless solid (Example 60).

Workup

  1. customThe hydrochloride (300 mg, 93%) thereupon precipitated as a diastereoisomer mixture with a melting point of 189°-194° C. in the form of a colourless solid (Example 60)

Sources & evidence

ORD record
ord-cd88ea623bc2446c9f5ac680313a61fa
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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