Chlorotrimethylsilane → 2-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[4-(1H-indol-3-yl)butyl]acetamide hydrochloride

HRID 908936Notes

Reaction equation

HRID 908936 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][C:6](=[CH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=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)[CH2:4][CH2:5][C:6](=[CH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)=[O:11])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 116770742-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[4-(1H-indol-3-yl)butyl]acetamide

Product 1

HCID 116770732-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[4-(1H-indol-3-yl)butyl]acetamide hydrochlorideYield 74%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[4-(1H-indol-3-yl)butyl]acetamide (184 mg, 0.428 mmol) was dissolved in ethyl methyl ketone (10 ml), and chlorotrimethylsilane (0.08 ml, 0.64 mmol) was added. After 1.5 h the hydrochloride was isolated as a colourless solid with an m.p. of 185-188° C. in a yield of 74% (147 mg).

Sources & evidence

ORD record
ord-4189cee6df21463e8521f158bcba58e1
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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