Reaction #5933

Reaction equation

3-(4-chlorophenyl)-1-[3-(methylamino)propyl]-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one

potassium carbonate

allyl bromide

→

1-[3-(N-allyl-N-methylamino)propyl]-3-(4-chlorophenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one

Solvents

acetone

Conditions

Workup

1. 1
   FiltrationThe insoluble materials are filtered off
2. 2
   workup.DISTILLATIONacetone is distilled off
3. 3
   Otherthe oily residue is purified by silica gel column chromatography (eluent, chloroform:methanol=20:1)

Procedure

To a mixture of 3-(4-chlorophenyl)-1-[3-(methylamino)propyl]-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (1.79 g), potassium carbonate (2.18 g) and acetone (50 ml) is added allyl bromide (0.65 g) under ice cooling, and the mixture is stirred at room temperature overnight. The insoluble materials are filtered off and acetone is distilled off, and the oily residue is purified by silica gel column chromatography (eluent, chloroform:methanol=20:1) to give 1-[3-(N-allyl-N-methylamino)propyl]-3-(4-chlorophenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one as oil.

Source