Chlorotrimethylsilane → {4-[4-(5-methoxy-1H-indol-3-yl)piperidine-1-yl]-1-phenylcyclohexyl}-dimethylamine dihydrochloride

HRID 2357437Notes

Reaction equation

HRID 2357437 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:13].Cl.[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH:26]1[CH2:31][CH2:30][N:29]([CH:32]2[CH2:37][CH2:36][C:35]([N:44]([CH3:46])[CH3:45])([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:34][CH2:33]2)[CH2:28][CH2:27]1.[Cl:47][Si](C)(C)C>CC(CC)=O>[ClH:47].[ClH:13].[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH:26]1[CH2:27][CH2:28][N:29]([CH:32]2[CH2:33][CH2:34][C:35]([N:44]([CH3:45])[CH3:46])([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:36][CH2:37]2)[CH2:30][CH2:31]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 10029113{4-[4-(5-methoxy-1H-indol-3-yl)piperidine-1-yl]-1-phenylcyclohexyl}-dimethylamine

Product 1

HCID 10029112{4-[4-(5-methoxy-1H-indol-3-yl)piperidine-1-yl]-1-phenylcyclohexyl}-dimethylamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To prepare the dihydrochloride the polar diastereoisomer of {4-[4-(5-methoxy-1H-indol-3-yl)piperidine-1-yl]-1-phenylcyclohexyl}-dimethylamine (170 mg, 0.4 mmole) was dissolved in ethyl methyl ketone (5 ml) and chlorotrimethylsilane (125 μl, 1.0 mmole) was added. The solid thereby formed was filtered off and dried. The polar {4-[4-(5-methoxy-1H-indol-3-yl)piperidine-1-yl]-1-phenylcyclohexyl}-dimethylamine dihydrochloride was thereby obtained as a colourless solid with an m.p. of 201°-203° C. in a yield of 200 mg (Example 8).

Workup

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

Sources & evidence

ORD record
ord-ba6d2c0f71c84f17bd2bdecc1785a5c4
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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