Hydrochloric Acid → HCID 19802037, compound

HRID 1646386Notes

Reaction equation

HRID 1646386 reaction equation
[C-:1]#[N:2].[Na+].[C:4]1([CH2:10][CH2:11][CH:12]=O)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:14][N:15]1[CH:20]([CH3:21])[CH2:19][CH2:18][CH2:17][CH:16]1[CH3:22].Cl>O.CO>[CH3:22][CH:16]1[CH2:17][CH2:18][CH2:19][CH:20]([CH3:21])[N:15]1[NH:14][CH:12]([CH2:11][CH2:10][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7707BenzenepropanalHCID 8929Sodium CyanideHCID 1234822,6-Dimethyl-1-piperidylamine

Product 1

HCID 19802037HCID 19802037, compoundYield 106.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 5.4 g of sodium cyanide in 20 ml of water and a solution of 14.7 g of 3-phenylpropionaldehyde in 15 ml of methanol are added dropwise with ice-cooling to a mixture of 12.8 g of 1-amino-2,6-dimethylpiperidine, 60 ml of water and 9.4 ml of concentrated hydrochloric acid. The pH is adjusted to 7 with hydrochloric acid and the reaction mixture is stirred at room temperature for 3 days. The mixture is extracted with dichloromethane, and the combined extracts are washed with water of pH 4 containing hydrochloric acid, dried and concentrated in a rotary evaporator. 28.9 g of 2-((2,6-dimethylpiperidino)amino)-4-phenylbutyronitrile are obtained, which are employed in the following step without further purification.

Workup

  1. extractionThe mixture is extracted with dichloromethane
  2. washthe combined extracts are washed with water of pH 4
  3. additioncontaining hydrochloric acid
  4. customdried
  5. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-54edf7146d1b42bf924629d86c6bf94d
Source dataset
uspto-grants-1993_01
Patent number
US05179206

Reaction notes

Loading…