Ammonia → 2-[4-(2-Ethoxyethyl)-2,3-dimethylphenoxy]ethanamine

HRID 1086661Notes

Reaction equation

HRID 1086661 reaction equation
N.[H][H].[CH3:4][C:5]1[C:15]([CH3:16])=[C:14]([CH2:17][CH2:18][O:19][CH2:20][CH3:21])[CH:13]=[CH:12][C:6]=1[O:7][CH2:8][CH:9]=[N:10]O>[Ni].CO>[CH3:4][C:5]1[C:15]([CH3:16])=[C:14]([CH2:17][CH2:18][O:19][CH2:20][CH3:21])[CH:13]=[CH:12][C:6]=1[O:7][CH2:8][CH2:9][NH2:10]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 72739086HCID 72739086, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 147712642-[4-(2-Ethoxyethyl)-2,3-dimethylphenoxy]ethanamineYield 85%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

Into a 20-liter autoclave charged were Raney nickel prepared (50 g as 50% alloy), 10 liters of methanol and 1.5 kg of liquid ammonia. After the hydrogen pressure was adjusted to 20 atm., the mixture was heated to 100° C. with stirring and stirred for one hour Into the mixture of activated Raney nickel thus obtained was charged 820 g of 2-[2,3-dimethyl-4-(2-ethoxyethyl)-phenoxy]-acetaldehyde oxime. Hydrogen was introduced until 20 atm., and the mixture was heated and stirred at 100° C. Absorption of hydrogen began at around 80° C. When the pressure was lowered, hydrogen was introduced to maintain the pressure at 20 atm. After about 0.5 to 2.5 hours, theoretical amount of hydrogen was absorbed, and then after cooling and releasing pressure, the catalyst was removed by filtration through a Nutze having Celite The filtrate was concentrated under reduced pressure to obtain a crude product. Yield 85-93%. The crude product was purified by distillation to obtain 2-[2,3-dimethyl-4-(2-ethoxyethyl)phenoxy]ethylamine (boiling point 170°-175° C./1 mmHg).

Workup

  1. additionInto a 20-liter autoclave charged
  2. customthus obtained
  3. temperaturethe mixture was heated
  4. stirringstirred at 100° C
  5. customAbsorption of hydrogen
  6. custombegan at around 80° C
  7. additionhydrogen was introduced
  8. temperatureto maintain the pressure at 20 atm
  9. customtheoretical amount of hydrogen was absorbed
  10. temperatureafter cooling
  11. customthe catalyst was removed by filtration through a Nutze
  12. concentrationwas concentrated under reduced pressure
  13. customto obtain a crude product
  14. distillationThe crude product was purified by distillation

Sources & evidence

ORD record
ord-2ff343e26d3c4842864d6920d90a7666
Source dataset
uspto-grants-1991_07
Patent number
US05030755

Reaction notes

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