Chlorotrimethylsilane → 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexylidene]-N-(3-phenylpropyl)acetamide Hydrochloride

HRID 908959Notes

Reaction equation

HRID 908959 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]1([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=2)[CH2:8][CH2:7][C:6](=[CH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:11])[CH2:5][CH2:4]1.C[Si](C)(C)[Cl:32]>CC(CC)=O>[ClH:32].[CH3:29][N:2]([CH3:1])[C:3]1([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=2)[CH2:8][CH2:7][C:6](=[CH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:11])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 11582801HCID 11582801, compound

Product 1

HCID 115828002-[4-dimethylamino-4-(3-fluorophenyl)cyclohexylidene]-N-(3-phenylpropyl)acetamide HydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-[4-Dimethylamino-4-(3-fluorophenyl)cyclohexylidene]-N-(3-phenylpropyl)acetamide (150 mg, 0.35 mmol) was dissolved in ethyl methyl ketone (10 ml) with gentle heating and trimethylchlorosilane (0.082 ml, 0.65 mmol) was added. After stirring at RT for 2 h, the reaction mixture was concentrated to dryness. The residue was stirred briefly with ether (10 ml) and the hydrochloride was isolated as a colourless solid with an m.p. of 230-233° C. in a yield of 98% (184 mg).

Workup

  1. temperaturewith gentle heating
  2. concentrationthe reaction mixture was concentrated to dryness
  3. stirringThe residue was stirred briefly with ether (10 ml)

Sources & evidence

ORD record
ord-65d81497252d442bac0241414e870686
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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