Sodium Hydroxide → HCID 22998298, compound

Temperature

95 °C

3-Chloro-10,11-dihydro-5H-dibenz[b,f]azepine (3.82 g, 16.6 mmol) was dissolved in toluene (20 ml). A solution of 3-chloropropionylchloride (2.53 g, 19.9 mmol) in toluene was added dropwise, and the resulting mixture was heated to 95° C. and stirred at that temperature for 30 minutes. The mixture was stirred overnight at room temperature. Further 3-chloropropionylchloride (2.53 g, 19.9 mmol) was added and the mixture was stirred at 95° C. for 1.5 h. After cooling, 0.2M sodium hydroxide (10 ml) was added, and the phases were separated. The organic phase was diluted with more toluene (50 ml), and washed with first 0.2M sodium hydroxide (6×10 ml) and then with more 0.2M sodium hydroxide (3×20 ml) until the water phase was alkaline. The organic phase was washed with water (3×15 ml), brine (25 ml), and dried (MgSO4). Evaporation in vacuo afforded 5.23 (98%) crude 3-chloro-1-(3-chloro-10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propanone as an oil. This was further purified by addition of a mixture of heptane and ethyl acetate (1:1). This afforded 3.14 g (59%) of the product as a solid.

1. stirringThe mixture was stirred overnight at room temperature
2. stirringthe mixture was stirred at 95° C. for 1.5 h
3. temperatureAfter cooling
4. customthe phases were separated
5. additionThe organic phase was diluted with more toluene (50 ml)
6. washwashed with first 0.2M sodium hydroxide (6×10 ml)
7. washThe organic phase was washed with water (3×15 ml), brine (25 ml)
8. dry with materialdried (MgSO4)
9. customEvaporation in vacuo

ORD record

ord-c18b281455914fce9b64c7c955712f40

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05962449