Reaction #93374

Reaction equation

alpha-isopropyl-alpha-[3-[N-[3-(3-hydroxymethylphenoxy)propyl]amino]propyl]-3,4,5-trimethoxyphenyl acetonitrile

formalin

sodium borohydride

→

desired compound

Yield 25.7%

Alpha-isopropyl-alpha-[3-[N-[3-(3-hydroxymethylphenoxy)propyl]-N-methylamino]propyl]-3,4,5-trimethoxyphenylacetonitrile

Yield 25.7%

Solvents

methanol

Conditions

Workup

1. 1
   TemperatureAfter cooling, to the solution
2. 2
   OtherThe solvent was removed and to the residue
3. 3
   workup.ADDITIONwas added water
4. 4
   ExtractionThe solution was extracted with chloroform
5. 5
   Washthe extract was washed with water
6. 6
   Otherdried
7. 7
   Otherevaporated
8. 8
   OtherThe residue was chromatographed on silica gel using 10% methanol-chloroform as an eluent

Procedure

A solution of 2.80 g of alpha-isopropyl-alpha-[3-[N-[3-(3-hydroxymethylphenoxy)propyl]amino]propyl]-3,4,5-trimethoxyphenyl acetonitrile and 4.84 g of 37% formalin in 70 ml of methanol was refluxed for 1 hour. After cooling, to the solution was added 2.25 g of sodium borohydride and the solution was stirred for 1 hour at room temperature. The solvent was removed and to the residue was added water. The solution was extracted with chloroform and the extract was washed with water, dried, and evaporated. The residue was chromatographed on silica gel using 10% methanol-chloroform as an eluent to give 0.74 g of the desired compound as a yellow oil.

Source