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

HRID 2357436Notes

Reaction equation

HRID 2357436 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 non-polar diastereoisomer of {4-[4-(5-methoxy-1H-indol-3-yl)piperidine-1-yl]-1-phenylcyclohexyl}-dimethylamine (590 mg, 1.37 mmole) was dissolved in ethyl methyl ketone (7 ml) and chlorotrimethylsilane (435 μl, 3.4 mmole) was added. The solid thereby formed was filtered off and dried. The non-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 224°-226° C. in a yield of 690 mg (100%)(Example 7).

Workup

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

Sources & evidence

ORD record
ord-e7f37b9caef04d1d97f30217b336dd21
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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