Chlorotrimethylsilane → 2-[4-Dimethylamino-4-(3-fluorophenyl)cyclohexylidene]-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide hydrochloride

HRID 908957Notes

Reaction equation

HRID 908957 reaction equation
C[Si](C)(C)[Cl:3].[CH3:6][N:7]([CH3:37])[C:8]1([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)[CH2:13][CH2:12][C:11](=[CH:14][C:15]([NH:17][CH:18]([CH3:29])[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:3].[CH3:37][N:7]([CH3:6])[C:8]1([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)[CH2:13][CH2:12][C:11](=[CH:14][C:15]([NH:17][CH:18]([CH3:29])[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 11712509HCID 11712509, compound

Product 1

HCID 117125082-[4-Dimethylamino-4-(3-fluorophenyl)cyclohexylidene]-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Trimethylchlorosilane (0.109 ml, 0.86 mmol) was added to a solution of the more polar diastereoisomer of 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexylidene]-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide (249 mg, 0.57 mmol) in ethyl methyl ketone (10 ml) and the mixture was stirred at RT for 1.5 h. The hydrochloride which had precipitated out was filtered off with suction and isolated as a colourless solid with an m.p. of 171-174° C. in a yield of 81% (218 mg) (Example 27).

Workup

  1. customThe hydrochloride which had precipitated out
  2. filtrationwas filtered off with suction
  3. customisolated as a colourless solid with an m.p. of 171-174° C. in a yield of 81% (218 mg) (Example 27)

Sources & evidence

ORD record
ord-002604bdb4c347398a10abbb558496e6
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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