Water → 4-{1-[Bis(2-chlorophenyl)-methyl)-piperidin-4-yl}-butyronitrile

HRID 1280775Notes

Reaction equation

HRID 1280775 reaction equation
Cl.[C:2]([CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)#[N:3].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:28])Br.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:28])[N:10]1[CH2:9][CH2:8][CH:7]([CH2:6][CH2:5][CH2:4][C:2]#[N:3])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 826777Bis(2-chlorophenyl)-bromomethaneHCID 184257044-(Piperidin-4-yl)butanenitrile hydrochloride

Product 1

HCID 184257454-{1-[Bis(2-chlorophenyl)-methyl)-piperidin-4-yl}-butyronitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

20 g (106 mmol) 4-(3-cyanoprop-1-yl)-piperidin hydrochloride, 40.2 g (127 mmol) bis(2-chlorophenyl)-bromomethane and 35.2 g (254 mmol) potassium carbonate are heated to boiling in 90 ml acetone for six hours. After cooling, the mixture is freed from solution under vacuum. The residue is dispersed between 90 ml tolueneand 90 ml water. The aqueous phase is extracted with 10 ml tolueneand the combined organic phases are washed with 10 ml water. The organic phase is concentrated and the residue is chromatographically purified over silica gel with CHCL3. Yield: 11.2 g (27%).

Workup

  1. temperatureAfter cooling
  2. additionThe residue is dispersed between 90 ml
  3. extractionThe aqueous phase is extracted with 10 ml tolueneand the combined organic phases
  4. washare washed with 10 ml water
  5. concentrationThe organic phase is concentrated
  6. customthe residue is chromatographically purified over silica gel with CHCL3

Sources & evidence

ORD record
ord-8bbe8f62ff014d25aab7bb8178ea63db
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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