Hydrochloric Acid → 2-((2,6-Dimethylpiperidino)amino)-3-methylbutyronitrile

HRID 1646384Notes

Reaction equation

HRID 1646384 reaction equation
[C-:1]#[N:2].[Na+].[CH:4](=O)[CH:5]([CH3:7])[CH3:6].[NH2:9][N:10]1[CH:15]([CH3:16])[CH2:14][CH2:13][CH2:12][CH:11]1[CH3:17].Cl>O.CO>[CH3:17][CH:11]1[CH2:12][CH2:13][CH2:14][CH:15]([CH3:16])[N:10]1[NH:9][CH:4]([CH:5]([CH3:7])[CH3:6])[C:1]#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6561IsobutyraldehydeHCID 8929Sodium CyanideHCID 1234822,6-Dimethyl-1-piperidylamine

Product 1

HCID 198020392-((2,6-Dimethylpiperidino)amino)-3-methylbutyronitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 4.9 g of sodium cyanide in 10 ml of water and a solution of 7.2 g of isobutyraldehyde in 30 ml of methanol are added dropwise with ice-cooling to a mixture of 6.4 g of 1-amino-2,6-dimethylpiperidine, 60 ml of water and 8.6 ml of concentrated hydrochloric acid. After stirring at room temperature for 8 days, the methanol is stripped off on a rotary evaporator and the solution is extracted with dichloromethane. The combined organic phases are washed with water of pH 5 containing acetic acid, dried and concentrated. 11.2 g of 2-((2,6-dimethylpiperidino)amino)-3-methylbutyronitrile remain, which are employed in the following step without further purification.

Workup

  1. customthe methanol is stripped off on a rotary evaporator
  2. extractionthe solution is extracted with dichloromethane
  3. washThe combined organic phases are washed with water of pH 5
  4. additioncontaining acetic acid
  5. customdried
  6. concentrationconcentrated
  7. customwhich are employed in the following step without further purification

Sources & evidence

ORD record
ord-c5b16b305d424d8f8eb99c380a0cb11b
Source dataset
uspto-grants-1993_01
Patent number
US05179206

Reaction notes

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