Propylamine → 4-n-Propylamino-cyclohexanone-ethyleneketal

HRID 1942391Notes

Reaction equation

HRID 1942391 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]2)[O:3][CH2:2]1.[CH2:12]([NH2:15])[CH2:13][CH3:14].[H][H]>CO.[Pd]>[O:3]1[C:4]2([CH2:9][CH2:8][CH:7]([NH:15][CH2:12][CH2:13][CH3:14])[CH2:6][CH2:5]2)[O:11][CH2:1][CH2:2]1

Participants

6

Reactant 3

HCID 7852PropylamineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 118200814-n-Propylamino-cyclohexanone-ethyleneketal

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 9.36 g (60 mmol) 1,4-cyclohexanedione monoethylene acetal in 60 mL of methanol and 9.84 mL (120 mmol) of propylamine is added 0.6 g of palladium on carbon (10%). The mixture is stirred overnight under 4 bar hydrogen pressure. Filtration over Celite and concentration in vacuum provides the crude product in almost quantitative yield.

Workup

  1. filtrationFiltration
  2. concentrationover Celite and concentration in vacuum

Sources & evidence

ORD record
ord-299e8384d5b94453bc80fc0b5d9181ac
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

Loading…