2,2,6,6-Tetramethyl-4-piperidone → 1,6-Bis(2,2,6,6-tetramethyl-4-piperidylamino)hexane

HRID 2260764Notes

Reaction equation

HRID 2260764 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.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH2:19].[H][H]>[Pt].CO>[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH:6]2[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3][C:2]([CH3:11])([CH3:1])[CH2:7]2)[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1

Participants

6

Reactant 3

HCID 132202,2,6,6-Tetramethyl-4-piperidoneHCID 16402HexamethylenediamineHCID 178418361HCID 178418361, compound

Product 1

HCID 934191,6-Bis(2,2,6,6-tetramethyl-4-piperidylamino)hexaneYield 90.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

In a 5 liter autoclave were charged 981 g (6.32 mols) of 2,2,6,6-tetramethyl-4-piperidone, 350 g (3.01 mols) of hexamethylenediamine, 1500 g of methanol and 5.0 g of 5% platinum on carbon with keeping the temperature at 45°-55° C. The inside of the autoclave was pressurized to 40 bars with hydrogen and heated to 70°-80° C. to carry out hydrogenation. The hydrogenation was completed after 4-5 hours. The catalyst was removed by filtration at 70°-80° C. under 2-3 bars and 1070 g of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,6-hexanediamine was obtained by distillation. Yield: 90%.

Workup

  1. customat 45°-55° C
  2. temperatureheated to 70°-80° C.
  3. customThe catalyst was removed by filtration at 70°-80° C. under 2-3 bars

Sources & evidence

ORD record
ord-4a04102d9e094b87b2ae59decae3f020
Source dataset
uspto-grants-1995_12
Patent number
US05478873

Reaction notes

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