Hydrochloric Acid → N-[(4-Dimethylamino-4-phenylcyclohexylcarbamoyl)methyl]-3-(1H-indol-3-yl)propionamide hydrochloride

HRID 1394246Notes

Reaction equation

HRID 1394246 reaction equation
Cl.[CH3:2][N:3]([CH3:34])[C:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:9][CH2:8][CH:7]([NH:10][C:11]([CH2:13][NH:14][C:15](=[O:27])[CH2:16][CH2:17][C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)=[O:12])[CH2:6][CH2:5]1.C[Si](C)(C)[Cl:37]>CC(CC)=O>[ClH:37].[CH3:34][N:3]([CH3:2])[C:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:9][CH2:8][CH:7]([NH:10][C:11]([CH2:13][NH:14][C:15](=[O:27])[CH2:16][CH2:17][C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)=[O:12])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 69216416N-[(4-dimethylamino-4-phenylcyclohexylcarbamoyl)methyl]-3-(1H-indol-3-yl)propionamide

Product 1

HCID 69217040N-[(4-Dimethylamino-4-phenylcyclohexylcarbamoyl)methyl]-3-(1H-indol-3-yl)propionamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In order to produce the hydrochloride (Example 12), the more polar diastereomer of N-[(4-dimethylamino-4-phenylcyclohexylcarbamoyl)methyl]-3-(1H-indol-3-yl)propionamide (257 mg, 0.57 mmole) was dissolved in ethyl methyl ketone and combined with trimethylchlorosilane (108 μl, 0.86 mmole). The resulting solid was filtered out and dried. Example 12 was obtained as a colorless solid (m.p. 135-137° C.) in a yield of 220 mg (79%).

Workup

  1. filtrationThe resulting solid was filtered out
  2. customdried

Sources & evidence

ORD record
ord-3f6bd26537ff47fb81bc6c5f60a26628
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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