Hydrochloric Acid → HCID 10109604, compound

4-Cyclohex-1-en-1-yl-benzoic acid of Step C (0.099 g, 0.489 mmol) and oxalyl chloride (0.065 g, 0.513 mmol) were dissolved in anhydrous methylene chloride (5 mL) and N,N-dimethylformamide (0.00114 mL, 0.0147 mmol) added. The resulting mixture was refluxed for 1 hour, then cooled to room temperature and solvent evaporated. The crude acid chloride thus prepared was combined with 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.090 g, 0.489 mmol) and N,N-diisopropyl ethylamine (0.103 mL, 0.589 mmol) in anhydrous dichloromethane (5 mL). After stirring at room temperature for 1.5 hours, 1 N hydrochloric acid (50 mL) was added and the resulting mixture extracted with diethyl ether (50 mL). The organic phase was washed with 1 N hydrochloric acid, 1 N sodium hydroxide and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated, and the residue purified by flash column chromatography on silica gel, eluting with 20% ethyl acetate in hexane. A slightly orange solid was isolated which was recrystallized from petroleum ether to afford the title compound (0.131 g) as white crystals, m.p. 156° C.

1. temperatureThe resulting mixture was refluxed for 1 hour
2. customsolvent evaporated
3. customThe crude acid chloride thus prepared
4. extractionthe resulting mixture extracted with diethyl ether (50 mL)
5. washThe organic phase was washed with 1 N hydrochloric acid, 1 N sodium hydroxide and brine
6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customthe residue purified by flash column chromatography on silica gel
10. washeluting with 20% ethyl acetate in hexane
11. customA slightly orange solid was isolated which
12. customwas recrystallized from petroleum ether

ORD record

ord-f3e87b5211444a0a9c12da232d5339e6

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07022699B2