Reaction #42389

Reaction equation

methyl 3-(hydroxymethyl)-5-methylbenzoate

methanesulfonyl chloride

N-methylbutylamine

→

title compound

Methyl 3-{[butyl(methyl)amino]methyl}-5-methylbenzoate

Solvents

methylene chloride

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   workup.STIRRINGthe reaction stirred at room temperature 16 h
3. 3
   ConcentrationThe solution is concentrated under reduced pressure
4. 4
   OtherPurification by flash chromatography

Procedure

To methyl 3-(hydroxymethyl)-5-methylbenzoate prepared by the method in Example SP-177 (1.1 g, 6.1 mmol), in anhydrous methylene chloride (10 mL) is added methanesulfonyl chloride (663 μL, 8.6 mmol) at −30° C., and the reaction is warmed to 0° C. The reaction stirred 1 h, then filtered. The filtrate is added to N-methylbutylamine (2.1 mL, 18.3 mmol), and the reaction stirred at room temperature 16 h. The solution is concentrated under reduced pressure. Purification by flash chromatography affords the title compound in pure form. ESI MS m/z 250.2 [M+H]+.

Source