Butylamine → n-Butyl-2,2,6,6-tetramethyl-4-piperidinamine

HRID 375771Notes

Reaction equation

HRID 375771 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][C:6](=O)[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.[CH2:12]([NH2:16])[CH2:13][CH2:14][CH3:15].[H][H]>CO.[Pt]=O>[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([NH:16][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1

Participants

6

Reactant 3

HCID 8007ButylamineHCID 132202,2,6,6-Tetramethyl-4-piperidoneHCID 178418361HCID 178418361, compound

Product 1

HCID 118285n-Butyl-2,2,6,6-tetramethyl-4-piperidinamineYield 95%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

155 g of 2,2,6,6-tetramethyl-4-piperidone and 80.0 g of butylamine were dissolved in 300 ml of methanol, and then 2.0 g of platinum oxide were added to the resulting solution, after which the solution was shaken under a pressure of 3 atmospheres of hydrogen in a medium-pressure hydrogenation apparatus at room temperature for 5 hours. At the end of this time, the platinum catalyst was filtered off, and the solvent was removed from the filtrate by distillation under reduced pressure, after which the residue was further purified by distillation under reduced pressure, to yield 201.5 g of the title compound as an oil boiling at 100° to 101° C./5 mmHg (667 Pa).

Workup

  1. filtrationAt the end of this time, the platinum catalyst was filtered off
  2. customthe solvent was removed from the filtrate by distillation under reduced pressure
  3. distillationafter which the residue was further purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-1602ad3f5da84801957bfb175f8bf42b
Source dataset
uspto-grants-1996_01
Patent number
US05486556

Reaction notes

Loading…