2-Methoxyethylamine → Benzenamine, N-(2-methoxyethyl)-2,6-dimethyl-

HRID 1448922Notes

Reaction equation

HRID 1448922 reaction equation
[CH3:1][C:2]1[C:3](=O)[CH:4]([CH3:8])[CH2:5][CH2:6][CH:7]=1.[CH3:10][O:11][CH2:12][CH2:13][NH2:14].C=CC>[Pd].C1(C)C=CC=CC=1>[CH3:10][O:11][CH2:12][CH2:13][NH:14][C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:8]

Participants

6

Reactant 3

HCID 80182-MethoxyethylamineHCID 8252PropyleneHCID 110946032,6-dimethyl-2-cyclohexen-1-one

Product 1

HCID 170858Benzenamine, N-(2-methoxyethyl)-2,6-dimethyl-Yield 34.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

2.0 g (0.0161 mole) of 2,6-dimethyl-cyclohex-2-en-1-one, 50 ml of toluene, 1.8 g (0.024 mole) of 2-methoxyethylamine and 0.5 g of palladium on charcoal (5%) are heated with a starting pressure of 17 bars (7 bars propylene and 10 bars nitrogen) for 10 hours at 180° C. After cooling, the catalyst is filtered off and the filter residue is washed with ether and toluene. The solvent is evaporated off to leave 1.0 g of crude N-(2-methoxyethyl)-2,6-dimethylaniline, from which is obtained, by distillation in high vacuum, 0.4 g (13% of theory) of pure N-(2-methoxyethyl)-2,6-dimethylaniline; b.p. 61°-62° C./ 0.1 Torr.

Workup

  1. temperatureAfter cooling
  2. filtrationthe catalyst is filtered off
  3. washthe filter residue is washed with ether and toluene
  4. customThe solvent is evaporated off

Sources & evidence

ORD record
ord-cc6b91ad073147dc91b982792b1dcbe9
Source dataset
uspto-grants-1980_02
Patent number
US04188341

Reaction notes

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