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

HRID 1975545Notes

Reaction equation

HRID 1975545 reaction equation
C[CH:2]([CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[CH:11]=1)S([O-])(=O)=O.[NH3:18].CS([O-])(=O)=O>CO>[CH3:17][C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([CH3:16])[CH:13]=1)[O:9][CH2:8][CH:7]([NH2:18])[CH3:2]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 85257MethanesulfonateHCID 86747580HCID 86747580, compound

Product 1

HCID 53052572-(3,5-Dimethyl-phenoxy)-1-methyl-ethylamineYield 86.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A 20 cc autoclave was charged with 5.42 g (21 mmol) of 1-methyl-2-(3,5-dimethylphenoxy)ethyl-methanesulfonate and 6 ml of methanol, and ammonia was added in an amount of 7.67 g which was 20 times, by mole, as much as the above methanesulfonate. The mixture was continuously stirred at 100° C. for 8 hours to finish the reaction. After the reaction mixture was allowed to cool, remaining ammonia was removed, and the reaction mixture was transferred into a 500 ml beaker with 50 ml of water and 20 ml of ethyl ether. A 20% hydrochloric acid aqueous solution was added until the reaction liquid was made acidic, and the reaction liquid was washed with 50 ml of diethyl ether three times. Then, while the water layer was cooled, a 20% sodium hydroxide aqueous solution was added to make it alkaline, and the reaction liquid was subjected to extraction with 50 ml of diethyl ether three times. The extract was dried over 10 g of anhydrous sodium sulfate, and the solvent was removed under reduced pressure to give 3.25 g of 1-(3,5-dimethylphenoxy)-2-aminopropane (boiling point 113° C./3 mmHg). This amount of 3.25 g corresponded to a yield of 86.6%, or was very high. The results of NMR and IR analyses were as follows.

Workup

  1. additionwas added in an amount of 7.67 g which
  2. customthe reaction
  3. temperatureto cool
  4. customwas removed
  5. additionA 20% hydrochloric acid aqueous solution was added until the reaction liquid
  6. customthe reaction liquid
  7. washwas washed with 50 ml of diethyl ether three times
  8. temperatureThen, while the water layer was cooled
  9. additiona 20% sodium hydroxide aqueous solution was added
  10. customthe reaction liquid
  11. extractionwas subjected to extraction with 50 ml of diethyl ether three times
  12. dry with materialThe extract was dried over 10 g of anhydrous sodium sulfate
  13. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ce4bdfbb790746e88773b6bfdf8adf80
Source dataset
uspto-grants-1994_02
Patent number
US05286905

Reaction notes

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