Diethyl Ether → 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)ethyl]acetamide Hydrochloride

HRID 908987Notes

Reaction equation

HRID 908987 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[O:11])[CH2:5][CH2:4]1.[Cl:32][Si](C)(C)C.CCOCC>CC(CC)=O>[ClH:32].[CH3:31][N:2]([CH3:1])[C:3]1([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[O:11])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 11655477HCID 11655477, compound

Product 1

HCID 116554762-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)ethyl]acetamide HydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The less polar diastereoisomer of 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)ethyl]acetamide (86 mg, 0.204 mmol) was dissolved in ethyl methyl ketone (5 ml), and chlorotrimethylsilane (0.038 ml, 0.3 mmol) was added. After 1 h ether (30 ml) was added to the reaction mixture and the mixture was stirred at RT for 30 min. The hydrochloride was isolated as a colourless solid in a yield of 94% (87 mg) with an m.p. of 135-140° C. (Example 50).

Sources & evidence

ORD record
ord-ee2050b344bf41049d9e8a142d7fba6e
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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