Chlorotrimethylsilane → HCID 10345215, compound

HRID 2357475Notes

Reaction equation

HRID 2357475 reaction equation
[CH3:1][N:2]([CH3:33])[C:3]1([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)[CH2:13]2)=[O:11])[CH2:5][CH2:4]1.[Cl:34][Si](C)(C)C>CC(CC)=O>[ClH:34].[CH3:33][N:2]([CH3:1])[C:3]1([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)[CH2:13]2)=[O:11])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 103452162-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone

Product 1

HCID 10345215HCID 10345215, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The non-polar diastereoisomer of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone (190 mg, 0.43 mmole) was dissolved in ethyl methyl ketone (10 ml) and chlorotrimethylsilane (0.08 ml, 0.63 mmole) was added. After a reaction time of 1.5 hours the hydrochloride was obtained in a yield of 100% (208 mg) as a colourless solid with an m.p. of 168°-173° C. (Example 40).

Sources & evidence

ORD record
ord-0daf7897d022486db0df50384231d20d
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

Loading…