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

HRID 2357469Notes

Reaction equation

HRID 2357469 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]([Cl:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:14]2)=[O:12])[CH2:6][CH2:5]1.Cl[Si](C)(C)C>CC(CC)=O>[ClH:28].[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]([Cl: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]([Cl: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 593855653-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amide

Product 2

HCID 593855653-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amideHCID 675326613-(5-chloro-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-chloro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amide (86 mg, 0.18 mmole) was dissolved in ethyl methyl ketone (3 ml) and chlorotrimethylsilane (34 μl, 0.27 mmole) was added. The solid thereby formed was filtered off and dried. The hydrochloride of the polar diastereoisomer of 3-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amide was thereby obtained in a yield of 92 mg (100%) as a colourless solid (Example 36) with an m.p. of 158°-160° C.

Workup

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

Sources & evidence

ORD record
ord-9c3468bb12b74f159696befb913fd031
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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