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

HRID 2357478Notes

Reaction equation

HRID 2357478 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][CH2:16][CH:15]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:14]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: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][CH2:16][CH:15]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:14]2)=[O:12])[CH2:6][CH2:5]1.[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][CH2:16][CH:15]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:14]2)=[O:12])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 593855673-(5-fluoro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amide

Product 2

HCID 593855673-(5-fluoro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amideHCID 675334143-(5-fluoro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amide hydrochloride

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To prepare the hydrochloride the polar diastereoisomer of 3-(5-fluoro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amide (200 mg, 0.43 mmole) was dissolved in ethyl methyl ketone (5 ml) and chlorotrimethylsilane (82 μl, 0.65 mmole) was added. The solid thereby formed was filtered off and dried. The hydrochloride of the polar diastereoisomer of 3-(5-fluoro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amide was thereby obtained as a colourless solid with an m.p. of 160°-164° C. in a yield of 215 mg (100%) (Example 42).

Workup

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

Sources & evidence

ORD record
ord-0e40b4c76a294f4dbbd6dabdd465ec91
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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