N,N-dimethyl-p-phenylenediamine → N,N-Dimethyl-1,4-cyclohexanediamine

HRID 1081470Notes

Reaction equation

HRID 1081470 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1>CC(O)=O.[Pd]>[CH3:1][N:2]([CH3:10])[CH:3]1[CH2:9][CH2:8][CH:6]([NH2:7])[CH2:5][CH2:4]1

Participants

4

Reactant 1

HCID 7472N,N-dimethyl-p-phenylenediamine

Product 1

HCID 345823N,N-Dimethyl-1,4-cyclohexanediamineYield 22.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 68 g of 4-dimethylaminoaniline and 34 g of 5% palladium-on-charcoal in 250 ml of AcOH is hydrogenated at a temperature of 75°-90° C. under a pressure of 50 bar. The catalyst is filtered off and washed with water and the filtrate is evaporated under vacuum. The residue is taken up with water, rendered alkaline by the addition of concentrated NaOH, extracted with AcOEt and dried over Na2SO4 and the solvent is evaporated off under vacuum. The oil obtained is distilled under reduced pressure to give 16.2 g of the expected product in the form of an oil. B.p.=102°-110° C. under 20 mm Hg.

Workup

  1. customis hydrogenated at a temperature of 75°-90° C. under a pressure of 50 bar
  2. filtrationThe catalyst is filtered off
  3. washwashed with water
  4. customthe filtrate is evaporated under vacuum
  5. additionby the addition of concentrated NaOH
  6. extractionextracted with AcOEt
  7. dry with materialdried over Na2SO4
  8. customthe solvent is evaporated off under vacuum
  9. customThe oil obtained
  10. distillationis distilled under reduced pressure

Sources & evidence

ORD record
ord-75ef320ccdf5430196a086a4ae70e317
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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