Reaction #1021

Reaction equation

ammonium acetate

sodium cyanoborohydride

3-(4-chlorophenoxy)-2-butanone

→

desired product

Yield 86.0%

2-(4-chlorophenoxy)-1-methylpropylamine

Yield 86.0%

Solvents

methanol

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was then concentrated under reduced pressure, and 180 mL of concentrated hydrochloric acid and 100 mL of water
2. 2
   workup.ADDITIONwere added to the residue
3. 3
   ExtractionThe whole mixture was extracted 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

82 g of ammonium acetate and 6.7 g of sodium cyanoborohydride were added to a solution containing 21 g of 3-(4-chlorophenoxy)-2-butanone dissolved in 500 mL of methanol, and the reaction mixture was stirred for 20 hours at room temperature. The reaction mixture was then concentrated under reduced pressure, and 180 mL of concentrated hydrochloric acid and 100 mL of water were added to the residue. The whole mixture was extracted with 300 mL of diethyl ether. The obtained water layer was alkalifled 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 18 g (yield 86%) of the desired product. Refractive index: 1.5360.

Source