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

HRID 1280776Notes

Reaction equation

HRID 1280776 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][C:18]#[N:19])[CH2:11][CH2:10]1.[H][H]>O1CCOCC1.C(O)C.[Ni]>[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 184257454-{1-[Bis(2-chlorophenyl)-methyl)-piperidin-4-yl}-butyronitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 184257064-{1-[Bis(2-chlorophenyl)methyl]-piperidin-4-yl}-butylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 22560076Dioxan ethanolSolvent

Procedure

8.0 g (20.6 mmol) 4-{1-[bis(2-chlorophenyl)-methyl]-piperidin-4-yl}-butyronitrile are dissolved in 240 ml dioxane/ethanol (1/5) and added to 1.5 g Raney-nickel. The mixture is stirred at RT under hydrogen atmosphere until uptake of the theoretical amount of hydrogen. The reaction solution is filtered from the catalyst and the solvent is removed under vacuum. The residue is dispersed between 100 ml 10% sodium hydroxide solution and 300 ml acetic acid ethyl ester. The organic phase is dried with sodium sulfate and the solvent is removed under vacuum. The resin is processed further without additional purification.

Workup

  1. filtrationThe reaction solution is filtered from the catalyst
  2. customthe solvent is removed under vacuum
  3. additionThe residue is dispersed between 100 ml 10% sodium hydroxide solution and 300 ml acetic acid ethyl ester
  4. dry with materialThe organic phase is dried with sodium sulfate
  5. customthe solvent is removed under vacuum
  6. customThe resin is processed further without additional purification

Sources & evidence

ORD record
ord-17c92918ac714b79886112038ef623a4
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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