2-Methylaziridine → 2-(3,5-Dimethyl-phenoxy)-1-methyl-ethylamine

HRID 1975533Notes

Reaction equation

HRID 1975533 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH3:10][CH:11]1[NH:13][CH2:12]1>C1(C)C=CC=CC=1.CCOCC>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH3:8])[CH:7]=1)[O:9][CH2:10][CH:11]([NH2:13])[CH3:12]

Participants

5

Reactant 2

HCID 63772-MethylaziridineHCID 79483,5-Dimethylphenol

Product 1

HCID 53052572-(3,5-Dimethyl-phenoxy)-1-methyl-ethylamineYield 69,107.102%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

24.4 Grams (0.20 mol) of 3,5-dimethylphenol and 3.8 g (0.067 mmol) of propyleneimine in 20 ml of toluene were allowed to react in an autoclave at 10 kg/cm2G at 200° C. for 1 hour. The reaction product was dispersed in 50 ml of ether, and then subjected to extraction with 50 ml of 5% hydrochloric acid three times. The water layer of the product was neutralized with sodium hydroxide, and the product was subjected to extraction with 50 ml of ether three times. The ether layer was washed and dried. Then, ether was distilled off, and the residue was distilled under reduced pressure to give 8.3 g of 1-(3,5-dimethylphenoxy)-2-propylamine as a component having a boiling point of 87° to 89° C./0.3 mmHg. Its yield was as high as 70%.

Workup

  1. customto react in an autoclave at 10 kg/cm2G at 200° C. for 1 hour
  2. extractionsubjected to extraction with 50 ml of 5% hydrochloric acid three times
  3. extractionthe product was subjected to extraction with 50 ml of ether three times
  4. washThe ether layer was washed
  5. customdried
  6. distillationThen, ether was distilled off
  7. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-c8182325a87b460c894a45c80f8e549c
Source dataset
uspto-grants-1994_02
Patent number
US05286905

Reaction notes

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