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

HRID 908988Notes

Reaction equation

HRID 908988 reaction equation
[Cl:1][Si](C)(C)C.[CH3:6][N:7]([CH3:36])[C:8]1([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=2)[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([NH:17][CH2:18][CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:16])[CH2:10][CH2:9]1>CC(CC)=O>[ClH:1].[CH3:36][N:7]([CH3:6])[C:8]1([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=2)[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([NH:17][CH2:18][CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:16])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 11655477HCID 11655477, compound

Product 1

HCID 116554762-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)ethyl]acetamide HydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Chlorotrimethylsilane (0.164 ml, 1.3 mmol) was added to a solution of the more polar diastereoisomer of 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)ethyl]acetamide (372 mg, 0.776 mmol) in ethyl methyl ketone (30 ml) and the mixture was stirred at RT for 1.5 h. The reaction mixture was concentrated to 10 ml, ether (60 ml) was added and the mixture was stirred at RT for 20 min. The hydrochloride was obtained as a colourless solid in a yield of 87% (348 mg) (Example 51).

Workup

  1. concentrationThe reaction mixture was concentrated to 10 ml, ether (60 ml)
  2. additionwas added
  3. stirringthe mixture was stirred at RT for 20 min

Sources & evidence

ORD record
ord-f3cd4cf7a72f45848ac2710f28ff4dbb
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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