Chlorotrimethylsilane → HCID 69217077, compound

HRID 1394260Notes

Reaction equation

HRID 1394260 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:8][CH2:7][CH:6]([NH:9][C:10]([NH:12][CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][CH:16]=2)=[O:11])[CH2:5][CH2:4]1.C[Si](C)(C)[Cl:34]>CC(CC)=O>[ClH:34].[CH3:31][N:2]([CH3:1])[C:3]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:4][CH2:5][CH:6]([NH:9][C:10]([NH:12][CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][CH:16]=2)=[O:11])[CH2:7][CH2:8]1.[CH3:31][N:2]([CH3:1])[C:3]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:4][CH2:5][CH:6]([NH:9][C:10]([NH:12][CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][CH:16]=2)=[O:11])[CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 69217077HCID 69217077, compound

Product 2

HCID 69217077HCID 69217077, compoundHCID 692198601-(4-Dimethylamino-4-phenylcyclohexyl)-3-[2-(5-fluoro-1H-indol-3-yl)ethyl]urea hydrochloride

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In order to produce the hydrochloride (compound 20), the more polar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexyl)-3-[2-(5-fluoro-1H-indol-3-yl)ethyl]urea (267 mg, 0.63 mmole) was dissolved in ethyl methyl ketone (5 ml) and combined with trimethylchlorosilane (120 μl, 0.95 mmole). The resulting solid was filtered out and dried. The hydrochloride of the more polar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexyl)-3-[2-(5-fluoro-1H-indol-3-yl)ethyl]urea was obtained in this manner as a colorless solid with a melting point of 219-221° C. in a yield of 290 mg (100%).

Workup

  1. filtrationThe resulting solid was filtered out
  2. customdried

Sources & evidence

ORD record
ord-c848920557a041a1bcc5cb0e9737fe8d
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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