2,2,6,6-Tetramethyl-4-piperidone → HCID 22902700, compound

HRID 484936Notes

Reaction equation

HRID 484936 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]([NH2:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CO.[Pt]=O>[CH2:12]([NH:24][CH:6]1[CH2:7][C:2]([CH3:11])([CH3:1])[NH:3][C:4]([CH3:10])([CH3:9])[CH2:5]1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 2

HCID 132202,2,6,6-Tetramethyl-4-piperidoneHCID 13583Dodecylamine

Product 1

HCID 22902700HCID 22902700, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

1.0 g of platinum oxide was added to a solution of 31.0 g of 2,2,6,6-tetramethyl-4-piperidone and 47.0 g of dodecylamine in 250 ml of methanol. The resulting mixture was then hydrogenated under a hydrogen atmosphere in a Parr hydrogenation apparatus at room temperature for 3 hours. After completion of the reaction, the platinum catalyst was filtered off, and then the solvent was distilled from the filtrate under reduced pressure to give an oily product. This product was purified by column chromatography through silica gel, eluted with a 20:3:1 by volume mixture of ethyl acetate, ethanol and triethylamine, to give the title compound as an oil. The Rf value of this product on thin layer chromatography was 0.34, using silica gel and a 20:3:1 by volume mixture of ethyl acetate, ethanol and triethylamine as the developing solvent.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe platinum catalyst was filtered off
  3. distillationthe solvent was distilled from the filtrate under reduced pressure
  4. customto give an oily product
  5. customThis product was purified by column chromatography through silica gel
  6. washeluted with a 20:3:1 by volume mixture of ethyl acetate, ethanol and triethylamine

Sources & evidence

ORD record
ord-88590e55aa714b46a303e90259d544b4
Source dataset
uspto-grants-1985_08
Patent number
US04533688

Reaction notes

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