Potassium Cyanide → 1-Benzyl-4-(dimethylamino)piperidine-4-carbonitrile

HRID 2212998Notes

Reaction equation

HRID 2212998 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:15]#[N:16].[K+].Cl.[CH3:19][NH:20][CH3:21]>C(O)C.O>[CH3:19][N:20]([CH3:21])[C:11]1([C:15]#[N:16])[CH2:12][CH2:13][N:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 10473Dimethylamine, hydrochlorideHCID 192201-Benzyl-4-piperidone

Product 1

HCID 164539151-Benzyl-4-(dimethylamino)piperidine-4-carbonitrileYield 96.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 1-(phenylmethyl)-4-piperidone (9.46 g, 50 mmol) in ethanol (20 mL) was added slowly to a stirred solution of potassium cyanide (3.58 g, 55 mmol) and dimethylamine hydrochloride (4.89 g, 60 mmol) in water (60 mL). The mixture was stirred at room temperature for 68 hours, then water (100 mL) was added. The solid was collected, suspended in aqueous sodium hydrogen carbonate (saturated, 100 mL) and water (50 mL) and extracted with dichloromethane (3×100 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the the title compound as a cream solid (11.69 g, 96%). m/z (ES+) 244 (M+1).

Workup

  1. customThe solid was collected
  2. extractionwater (50 mL) and extracted with dichloromethane (3×100 mL)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-291adae48e0342db817d4c15949f9bac
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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