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

HRID 2357473Notes

Reaction equation

HRID 2357473 reaction equation
[CH3:1][N:2]([CH3:32])[C:3]1([C:26]2[CH:31]=[CH:30][CH:29]=[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:33][Si](C)(C)C>CC(CC)=O>[ClH:33].[CH3:32][N:2]([CH3:1])[C:3]1([C:26]2[CH:27]=[CH:28][CH:29]=[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 100047112-(4-dimethylamino-4-phenylcyclohexyl)-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone

Product 1

HCID 100047102-(4-dimethylamino-4-phenylcyclohexyl)-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone hydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-(4-dimethylamino-4-phenylcyclohexyl)-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone (510 mg, 1.19 mmole) was dissolved in ethyl methyl ketone (15 ml) and chlorotrimethylsilane (0.226 ml, 1.8 mmole) was added. After 1 hour the hydrochloride was isolated as a colourless compound with an m.p. of 180°-191° C. in a yield of 94% (523 mg) (Example 39).

Sources & evidence

ORD record
ord-d57940d5f47b4b48a1d3230b2baf2824
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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