Hydrochloric Acid → HCID 18917626, compound

2-Amino-4-decylbenzophenone (4.16 g) was dissolved in chloroform (40 ml) and phthaloylalanyl chloride (3.22 g) was added thereto with stirring at room temperature. The mixture was stirred for 0.5 hour. The reaction mixture was washed with 5% aqueous sodium hydrogencarbonate and water and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography and the oily substance obtained was dissolved in a mixed solvent of methanol (20 ml) and tetrahydrofuran (40 ml). Thereto was added hydrazine monohydrate (1.56 g) with stirring under ice-cooling and the mixture was stirred for 2 hours. Conc. hydrochloric acid (1 ml) was added thereto with stirring at room temperature and the mixture was stirred at 60° C. for 2 hours. After cooling, the mixture was concentrated under reduced pressure and the residue was extracted with chloroform and washed with 5% aqueous sodium hydrogencarbonate and water. The residue was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. Isopropyl alcohol (60 ml) and acetic acid (1 ml) were added to the concentrate and the mixture was stirred at 70° C. for 1 hour. After cooling, the residue obtained by concentration under reduced pressure was extracted with chloroform and washed with 5% aqueous sodium hydrogencarbonate and water. The extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to give 3.2 g of 8-decyl-1,3-dihydro-3-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one as crystals.

1. stirringThe mixture was stirred for 0.5 hour
2. washThe reaction mixture was washed with 5% aqueous sodium hydrogencarbonate and water
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationAfter filtration
5. concentrationthe filtrate was concentrated under reduced pressure
6. customThe concentrate was purified by silica gel column chromatography
7. customthe oily substance obtained
8. stirringwith stirring under ice-
9. temperaturecooling
10. stirringthe mixture was stirred for 2 hours
11. stirringwith stirring at room temperature
12. stirringthe mixture was stirred at 60° C. for 2 hours
13. temperatureAfter cooling
14. concentrationthe mixture was concentrated under reduced pressure
15. extractionthe residue was extracted with chloroform
16. washwashed with 5% aqueous sodium hydrogencarbonate and water
17. dry with materialThe residue was dried over anhydrous sodium sulfate
18. filtrationAfter filtration
19. concentrationthe filtrate was concentrated under reduced pressure
20. additionIsopropyl alcohol (60 ml) and acetic acid (1 ml) were added to the
21. concentrationconcentrate
22. stirringthe mixture was stirred at 70° C. for 1 hour
23. temperatureAfter cooling
24. customthe residue obtained by concentration under reduced pressure
25. extractionwas extracted with chloroform
26. washwashed with 5% aqueous sodium hydrogencarbonate and water
27. dry with materialThe extract was dried over anhydrous sodium sulfate
28. filtrationAfter filtration
29. concentrationthe filtrate was concentrated under reduced pressure
30. custompurified by silica gel column chromatography

ORD record

ord-b7113562eab34025872b65c2ebc3b10b

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05753649