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

HRID 1394254Notes

Reaction equation

HRID 1394254 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.NC(N)=O.C[Si](C)(C)[Cl:39]>CC(CC)=O>[ClH:39].[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 1176UreaHCID 6397ChlorotrimethylsilaneHCID 692170381-(4-dimethylamino-4-phenylcyclohexyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]urea hydrochloride

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 1-(4-dimethylamino-4-phenylcyclohexyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]urea hydrochloride (Example 17), the more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexyl)-3-[2-1H-indol-3-yl)-1-methylethyl]urea (125 mg, 0.3 mmole) was dissolved in ethyl methyl ketone (3 ml) and combined with trimethylchlorosilane (57 μl, 0.45 mmole). The resulting solid was filtered out and dried. The hydrochloride of the more nonpolar 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 154-156° C. in a yield of 135 mg (100%).

Workup

  1. filtrationThe resulting solid was filtered out
  2. customdried

Sources & evidence

ORD record
ord-9f4c2278048e4c23a8ba24750048c28c
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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