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

HRID 2357441Notes

Reaction equation

HRID 2357441 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:13].Cl.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH:24]2[CH2:29][CH2:28][CH2:27][N:26]([CH:30]3[CH2:35][CH2:34][C:33]([N:42]([CH3:44])[CH3:43])([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH2:32][CH2:31]3)[CH2:25]2)=[CH:16]1.[Cl:45][Si](C)(C)C>CC(CC)=O>[ClH:45].[ClH:13].[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH:24]2[CH2:29][CH2:28][CH2:27][N:26]([CH:30]3[CH2:35][CH2:34][C:33]([N:42]([CH3:44])[CH3:43])([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH2:32][CH2:31]3)[CH2:25]2)=[CH:16]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 57438232{4-[3-(1H-indol-3-yl)piperidine-1-yl]-1-phenylcyclohexyl}-dimethylamine

Product 1

HCID 67532584{4-[3-(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-[3-(1H-indol-3-yl)piperidine-1-yl]-1-phenylcyclohexyl}-dimethylamine (208 mg, 0.52 mmole) was dissolved in ethyl methyl ketone (5 ml) and chlorotrimethylsilane (165 μl, 1.3 mmole) was added. The solid thereby obtained was filtered off and dried. The non-polar {4-[3-(1H-indol-3-yl)piperidine-1-yl]-1-phenylcyclohexyl}-dimethylamine dihydrochloride was thereby obtained as a colourless solid with an m.p. of 188°-190° C. in a yield of 245 mg (100%) (Example 9).

Workup

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

Sources & evidence

ORD record
ord-515b6b68c437472289eda9bf7ccf8f49
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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