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

HRID 704159Notes

Reaction equation

HRID 704159 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. stirringstirred for one hour
  3. customthus obtained
  4. temperaturethe mixture was heated
  5. stirringstirred at 100° C
  6. customAbsorption of hydrogen
  7. custombegan at around 80° C
  8. additionhydrogen was introduced
  9. temperatureto maintain the pressure at 20 atm
  10. customtheoretical amount of hydrogen was absorbed
  11. temperatureafter cooling
  12. customthe catalyst was removed by filtration through a Nutze
  13. concentrationThe filtrate was concentrated under reduced pressure
  14. customto obtain a crude product
  15. distillationThe crude product was purified by distillation

Sources & evidence

ORD record
ord-95c58a42fa104bb39bda8dbcc29205f3
Source dataset
uspto-grants-1991_01
Patent number
US04985596

Reaction notes

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