Reacción #4957

Ecuación de reacción

azetidine

potassium carbonate

azetidine

2-(2-chloroethyl)-2,5-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione

dimethylsulfoxide

azetidine

→

pale yellow crystals

Rendimiento 31.0%

2-[2-(1-Azetidinyl)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-thione fumarate

Rendimiento 31.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred overnight at room temperature
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued for 24 hr
4. 4
   FiltraciónThe mixture was filtered
5. 5
   Otrosolvent removed by rotary evaporator at 80° C.
6. 6
   Lavadothe solution was washed with two 30 ml portions of dilute aqueous sodium hydroxide
7. 7
   SecadoThe organic layer was dried over magnesium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated by rotary evaporator
10. 10
    OtroThe residue was reacted with fumaric acid in isopropyl alcohol

Procedimiento

To 5.0 g (0.0914 mole) of 2-(2-chloroethyl)-2,5-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione dissolved in 50 ml of dimethylsulfoxide was added 8.04 g (0.058 mole) of potassium carbonate and 1.21 g (0.021 mole) of azetidine. The reaction mixture was stirred at room temperature for 8 hr after which was added 0.5 g (0.009 mole) of azetidine and the mixture was stirred overnight at room temperature. An additional 0.3 g (0.005 mole of azetidine was added and stirring was continued for 24 hr. The mixture was filtered and solvent removed by rotary evaporator at 80° C., 0.5 mm Hg. The residue was taken up in 100 ml of chloroform and the solution was washed with two 30 ml portions of dilute aqueous sodium hydroxide. The organic layer was dried over magnesium sulfate, filtered and concentrated by rotary evaporator. The residue was reacted with fumaric acid in isopropyl alcohol to give 2.5 g (31%) of pale yellow crystals, m.p. 122°-126° C.

Fuente