Hydrochloric Acid → 4-(5-fluoro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amide hydrochloride

HRID 2357466Notes

Reaction equation

HRID 2357466 reaction equation
Cl.[CH3:2][N:3]([CH3:35])[C:4]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:9][CH2:8][CH:7]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH2:6][CH2:5]1.[Cl:36][Si](C)(C)C>CC(CC)=O>[ClH:36].[CH3:2][N:3]([CH3:35])[C:4]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:9][CH2:8][CH:7]([NH:10][C:11]([N:13]2[CH2:14][CH2:15][CH:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:17][CH2:18]2)=[O:12])[CH2:6][CH2:5]1.[CH3:2][N:3]([CH3:35])[C:4]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:9][CH2:8][CH:7]([NH:10][C:11]([N:13]2[CH2:14][CH2:15][CH:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:17][CH2:18]2)=[O:12])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 10436023HCID 10436023, compound

Product 2

HCID 104360224-(5-fluoro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amide hydrochlorideHCID 10436023HCID 10436023, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To prepare the hydrochloride the non-polar diastereoisomer of 4-(5-fluoro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amide (220 mg, 0.48 mmole) was dissolved in ethyl methyl ketone (5 ml) and chlorotrimethylsilane (92 μl, 0.71 mmole) was added. The solid thereby formed was filtered off and dried. The hydrochloride of the non-polar diastereoisomer of 4-(5-fluoro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amide was thereby obtained in a yield of 237 mg (100%) as a colourless solid (Example 33) with an m.p. of 167°-170° C.

Workup

  1. customThe solid thereby formed
  2. filtrationwas filtered off
  3. customdried

Sources & evidence

ORD record
ord-f43b9f1942fd4defb60179e178dca389
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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