Reaction #1020

Reaction equation

ammonium acetate

sodium cyanoborohydride

(4-chloro-2-methylphenoxy)acetone

→

desired product

Yield 81.0%

2-(4-chloro-2-methylphenoxy)-1-methylethylamine

Yield 81.0%

Solvents

methanol

Conditions

Workup

1. 1
   ConcentrationAfter the reaction mixture was concentrated under reduced pressure
2. 2
   workup.ADDITION180 mL of concentrated hydrochloric acid and 100 mL of water were added to the residue
3. 3
   Extractionextracted with 300 mL of diethyl ether
4. 4
   Extractionextracted with 500 mL of ethyl acetate
5. 5
   WashThe organic layer was washed with water
6. 6
   Dryingdried over anhydrous magnesium sulfate
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   Otherwas removed from the obtained oily products

Procedure

120 g of ammonium acetate and 9.8 g of sodium cyanoborohydride were added to a solution containing 31 g of (4-chloro-2-methylphenoxy)acetone dissolved in 700 mL of methanol, and the resultant mixture was stirred for 20 hours at room temperature. After the reaction mixture was concentrated under reduced pressure. 180 mL of concentrated hydrochloric acid and 100 mL of water were added to the residue. The whole mixture was stirred for 1 hour, and then extracted with 300 mL of diethyl ether. The water layer was alkalified using a 5% aqueous solution of sodium hydroxide, and then extracted with 500 mL of ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. A fraction possessing a low boiling point was removed from the obtained oily products to afford 25 g (yield 81%) of the desired product. Refractive index: 1.5360.

Source