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

HRID 2357442Notes

Reaction equation

HRID 2357442 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 polar dihydrochloride the polar diastereoisomer of {4-[3-(1H-indol-3-yl)piperidine-1-yl]-1-phenylcyclohexyl}-dimethylamine (50 mg, 0.12 mmole) was dissolved in ethyl methyl ketone (3 ml) and chlorotrimethylsilane (40 μl, 0.03 mmole) was added. The solid thereby formed was filtered off and dried. The 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 186-188° C. in a yield of 59 mg (100%) (Example 10).

Workup

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

Sources & evidence

ORD record
ord-df54143e41ac46da9deddd5774cf6d2b
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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