1-(3,5-Dimethylphenoxy)-2-propanone oxime → 2-(3,5-Dimethyl-phenoxy)-1-methyl-ethylamine
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([CH3:14])[CH:13]=1)[O:5][CH2:6][C:7](=[N:9]O)[CH3:8]>C(O)C.[Ni]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([CH3:14])[CH:13]=1)[O:5][CH2:6][CH:7]([NH2:9])[CH3:8]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
10.0 Grams (52 mmol) of 1-(3,5-dimethylphenoxy)-2-propanone oxime was dissolved in 50 ml of ethanol in an autoclave, and 1.0 g of a Raney nickel catalyst (W-2) was added. The resultant mixture was stirred under a hydrogen pressure of 5 kg/cm2G at 50° to 60° C. for 1 hour. The catalyst was separated by filtration, and the filtrate was concentrated under reduced pressure. The residue was dissolved in 50 ml of ethyl ether, and the mixture was subjected to extraction with a 20% hydrochloric acid aqueous solution. The extracted water layer was made alkaline with a 20% sodium hydroxide aqueous solution, and subjected to extraction with 50 ml of ethyl ether. The extracted organic layer was distilled under reduced pressure to give 8.01 g (yield 86%) of 1-(3,5-dimethylphenoxy)2-aminopropane (boiling point 113° C./3 mmHg).
Workup
- additionwas added
- customThe catalyst was separated by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- dissolutionThe residue was dissolved in 50 ml of ethyl ether
- extractionthe mixture was subjected to extraction with a 20% hydrochloric acid aqueous solution
- extractionsubjected to extraction with 50 ml of ethyl ether
- distillationThe extracted organic layer was distilled under reduced pressure
Sources & evidence
- ORD record
- ord-a702c35e5151447aac5eba41099f7a81
- Source dataset
- uspto-grants-1994_02
- Patent number
- US05286905
Reaction notes
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