Hexamethylenediamine → HCID 21182128, compound

HRID 1590940Notes

Reaction equation

HRID 1590940 reaction equation
[CH:1]1([O:7][N:8]2[C:13]([CH3:15])([CH3:14])[CH2:12][C:11](=O)[CH2:10][C:9]2([CH3:18])[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:19]([NH2:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH2:25]>[Pt]=O.C(O)C>[CH:1]1([O:7][N:8]2[C:9]([CH3:18])([CH3:17])[CH2:10][CH:11]([NH:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][NH:26][CH:11]3[CH2:12][C:13]([CH3:15])([CH3:14])[N:8]([O:7][CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[C:9]([CH3:18])([CH3:17])[CH2:10]3)[CH2:12][C:13]2([CH3:15])[CH3:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 16402HexamethylenediamineHCID 22019868N-cyclohexyloxy-4-oxo-2,2,6,6-tetramethylpiperidine

Product 1

HCID 21182128HCID 21182128, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 15.0 g (59.1 mmol) of 1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-one, 3.4 g (29.6 mmol) of 1,6-hexanediamine, 500 mg of platinum oxide, and 150 ml of ethanol is hydrogenated in a Paar apparatus for 4 hours. The catalyst is removed by filtration. The filtrate is concentrated to an oil which is purified by flash chromatography (silica gel:ethyl acetate, then ethyl acetate:methanol) to afford 9.7 g {55% yield) of the title compound, as a yellow oil.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationThe filtrate is concentrated to an oil which
  3. customis purified by flash chromatography (silica gel

Sources & evidence

ORD record
ord-0f46801b0a8948739db60776ad19a6b5
Source dataset
uspto-grants-1993_04
Patent number
US05204473

Reaction notes

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