Tetrahydrofuran → HCID 20256868, compound

To a solution of 11.8 g. of α-(m-chlorophenyl)-4-morpholineacetonitrile in 50 ml. of tetrahydrofuran is added 60 drops of a 30% solution of KOH in methanol. To the solution is added 4.62 ml. of methacrylonitrile (temperature rose to 42° C.). After stirring for 1 hr., the mixture is concentrated to dryness and the residue dissolved in methylene chloride. The solution is passed through a short column of hydrous magnesium silicate and the eluent concentrated to give 15.5 g. of a yellow oil. The oil is heated (steam bath) with a mixture of 75 ml. of acetic acid and 5 ml. of water for 1 hr. and the solvent removed under vacuum. Addition of water to the residue gives 11.2 g. of crystals, m.p. 72°-75° C. Recrystallization from methylene chloride-hexane gives 8.95 g. of crystals, m.p. 79.5°-80.5° C.

1. additionTo the solution is added 4.62 ml
2. concentration, the mixture is concentrated to dryness
3. dissolutionthe residue dissolved in methylene chloride
4. concentrationthe eluent concentrated
5. customto give 15.5 g
6. temperatureThe oil is heated (steam bath)
7. additionwith a mixture of 75 ml
8. customand the solvent removed under vacuum
9. additionAddition of water to the residue
10. customgives 11.2 g
11. customRecrystallization from methylene chloride-hexane
12. customgives 8.95 g

ORD record

ord-34588d2c589846f7a57b9da4bc0b62ab

Source dataset

uspto-grants-1978_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04112095