Ammonia → 2,6-Diethyl-2,3,6-trimethylpiperidin-4-amine

HRID 1701103Notes

Reaction equation

HRID 1701103 reaction equation
[CH2:1]([C:3]1([CH3:14])[CH:8]([CH3:9])[C:7](=O)[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2].[NH3:15].[H][H]>CO.[Ni]>[CH2:1]([C:3]1([CH3:14])[CH:8]([CH3:9])[CH:7]([NH2:15])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 221822132,6-Diethyl-2,3,6-trimethylpiperidin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 224860192,6-Diethyl-2,3,6-trimethylpiperidin-4-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

197.3 g of 2,6-diethyl-2,3,6-trimethylpiperidin-4-one are dissolved in 1.5 liters of methanol which is saturated with ammonia. This solution is hydrogenated in a 3 liter-autoclave at a hydrogen pressure of 100 bar in the presence of 30 g of Raney nickel. After 24 hours, the solution is filtered and the solvent evaporated. The residue is distilled in vacuo yielding 162 g 2,6-diethyl-2,3,6-trimethyl-4-aminopiperidine (compound no. 1) distilling at 133°-35° C. at 23 mm Hg. Using a methanolic solution of methylamine, n-butylamine, n-hexylamine, n-dodecylamine, benzylamine and 2-amino-ethanol, respectively, instead of the ammonia solution while otherwise following the procedure described above, there are obtained:

Workup

  1. filtrationthe solution is filtered
  2. customthe solvent evaporated
  3. distillationThe residue is distilled in vacuo

Sources & evidence

ORD record
ord-febe0f886c384ae7a33273452e9d3ab4
Source dataset
uspto-grants-1980_03
Patent number
US04191683

Reaction notes

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