Hydrochloric Acid → 1-(4-dimethylamino-4-phenylcyclohexyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]urea

HRID 1394255Notes

Reaction equation

HRID 1394255 reaction equation
Cl.[CH3:2][N:3]([CH3:32])[C:4]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:9][CH2:8][CH:7]([NH:10][C:11]([NH:13][CH:14]([CH3:25])[CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:12])[CH2:6][CH2:5]1.C[Si](C)(C)[Cl:35]>CC(CC)=O>[ClH:35].[CH3:32][N:3]([CH3:2])[C:4]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:5][CH2:6][CH:7]([NH:10][C:11]([NH:13][CH:14]([CH3:25])[CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:12])[CH2:8][CH2:9]1.[CH3:32][N:3]([CH3:2])[C:4]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:5][CH2:6][CH:7]([NH:10][C:11]([NH:13][CH:14]([CH3:25])[CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:12])[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 692169201-(4-dimethylamino-4-phenylcyclohexyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]urea

Product 2

HCID 692169201-(4-dimethylamino-4-phenylcyclohexyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]ureaHCID 692170381-(4-dimethylamino-4-phenylcyclohexyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]urea hydrochloride

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In order to produce the hydrochloride (Example 18), the more polar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]urea (100 mg, 0.24 mmole) was dissolved in ethyl methyl ketone (3 ml) and combined with trimethylchlorosilane (46 μl, 0.36 mmole). The resulting solid was filtered out and dried. The hydrochloride of the more polar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]urea was obtained in this manner as a colorless solid with a melting point of 175-177° C. in a yield of 108 mg (100%).

Workup

  1. filtrationThe resulting solid was filtered out
  2. customdried

Sources & evidence

ORD record
ord-fab3bc409b014ca98230d75c7a5f423e
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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