Reaction #5932

Reaction equation

3-(3-trifluoromethylphenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one

potassium carbonate

3-(dimethylamino)propyl chloride hydrochloride

acetone

→

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

Solvents

water

Conditions

Workup

1. 1
   Temperatureis refluxed for 48 hours
2. 2
   FiltrationThe insoluble materials are filtered off
3. 3
   workup.DISTILLATIONacetone is distilled off
4. 4
   workup.ADDITIONto the residue are added ethanol (200 ml) and 10 % hydrochloric acid (100 ml)
5. 5
   Temperaturethe mixture is refluxed for one hour
6. 6
   workup.DISTILLATIONAfter ethanol is distilled off
7. 7
   Filtrationthe insoluble materials are filtered off
8. 8
   Extractionextracted with ethyl acetate
9. 9
   workup.DISTILLATIONThe extract is distilled
10. 10
    Otherto remove the solvent

Procedure

A mixture of 3-(3-trifluoromethylphenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (18.0 g), potassium carbonate (24.2 g), 3-(dimethylamino)propyl chloride hydrochloride (9.5 g), acetone (400 ml) and water (4 ml) is refluxed for 48 hours. The insoluble materials are filtered off and acetone is distilled off, and to the residue are added ethanol (200 ml) and 10 % hydrochloric acid (100 ml), and the mixture is refluxed for one hour. After ethanol is distilled off and the insoluble materials are filtered off, the resulting mixture is made alkaline with sodium hydrogen carbonate and extracted with ethyl acetate. The extract is distilled to remove the solvent to give 1-[3-(dimethylamino)-propyl]-3-(3-trifluoromethylphenyl)-1H-naphtho[2,1-b][1,4]-thiazin-2(3H)-one as oil.

Source