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

HRID 2357471Notes

Reaction equation

HRID 2357471 reaction equation
Cl.[CH3:2][N:3]([CH3:36])[C:4]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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]([O:28][CH3:29])[CH:26]=4)[NH:21][CH:20]=3)[CH2:14]2)=[O:12])[CH2:6][CH2:5]1.[Cl:37][Si](C)(C)C>CC(CC)=O>[ClH:37].[CH3:36][N:3]([CH3:2])[C:4]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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]([O:28][CH3:29])[CH:26]=4)[NH:21][CH:20]=3)[CH2:14]2)=[O:12])[CH2:6][CH2:5]1.[CH3:36][N:3]([CH3:2])[C:4]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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]([O:28][CH3:29])[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 593855613-(5-methoxy-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amide

Product 2

HCID 593855613-(5-methoxy-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amideHCID 675321573-(5-methoxy-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 non-polar diastereoisomer of 3-(5-methoxy-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amide (244 mg, 0.51 mmole) was dissolved in ethyl methyl ketone (5 ml) and chlorotrimethylsilane (98 μl, 0.77 mmole) was added. The solid thereby formed was filtered off and dried. The hydrochloride of the non-polar diastereoisomer of 3-(5-methoxy-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl)-amide was thereby obtained in a yield of 262 mg (100%) as a colourless solid (Example 37) with an m.p. of 160°-162° C.

Workup

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

Sources & evidence

ORD record
ord-063692fea1b8469198bfef674d3bb5f7
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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