Reaction #1637

Reaction equation

(S)-1-(4-benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol

benzyl bromide

sodium carbonate

→

title compound

(S)-N-Benzyl-1(4-benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol

Solvents

dimethylformamide

Conditions

Workup

1. 1
   FiltrationThe mixture was filtered
2. 2
   Washthe residue was washed with ethyl acetate
3. 3
   Washwashed with water and brine
4. 4
   Otherdried
5. 5
   Otherevaporated
6. 6
   OtherPurification of the residue by flash chromatography (silica gel, 50% ethyl acetate in hexane)

Procedure

A solution of (S)-1-(4-benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol (1.9 g, 4.8 mMol) and benzyl bromide (0.57 ml, 4.8 mMol) in dimethylformamide (10 ml) containing sodium carbonate (770 mg, 7.2 mMol) was stirred at room temperature for 18 hours. The mixture was filtered and the residue was washed with ethyl acetate. The filtrates were combined, washed with water and brine, dried and evaporated. Purification of the residue by flash chromatography (silica gel, 50% ethyl acetate in hexane) gave the title compound.

Source