Reaction #2045050

Reaction equation

Benzyloxyacetyl chloride

6-(4-aminophenoxy)hexanoic acid methyl ester

6-(4-Amino-phenoxy)-hexanoic acid methyl ester

triethylamine

→

70

Yield 22.2%

6-[4-(2-Benzyloxyacetylamino)phenoxy]hexanoic acid methyl ester

Yield 22.2%

Solvents

acetone

Conditions

Workup

1. 1
   FiltrationSolids were filtered off
2. 2
   workup.DISTILLATIONacetone distilled off
3. 3
   workup.ADDITIONwater (100 ml) added
4. 4
   ExtractionCrude 70 was extracted into chloroform
5. 5
   Washwashed with 5% sodium bicarbonate solution (2×100 ml), water (100 ml)
6. 6
   Dryingdried over sodium sulphate
7. 7
   workup.DISTILLATIONdistilled
8. 8
   OtherCrude 70 was purified by column chromatography on silica gel

Procedure

Benzyloxyacetyl chloride (25 gm, 135.5 mmol) was added dropwise to a mixture of 6-(4-aminophenoxy)hexanoic acid methyl ester 21 (25 g, 105 mmol) and triethylamine (21.4 g, 211.6 mmol) in acetone (200 ml) at 0° C. and stirred at room temp. for 12 hrs. Solids were filtered off, acetone distilled off and water (100 ml) added. Crude 70 was extracted into chloroform, washed with 5% sodium bicarbonate solution (2×100 ml), water (100 ml), dried over sodium sulphate and distilled. Crude 70 was purified by column chromatography on silica gel using benzene as eluant to get pure 70 (9 g, 22.2%) as a off-white powder. M.p: 46-49° C.

Source