Benzyl Alcohol → HCID 178478168, compound

Temperature

50 °C

A mixture of dry DMF (5 ml), benzylalcohol (216 mg, 2.0 mmol) and 60% sodium hydride (80 mg, 2.0 mmol) placed under an atmosphere of nitrogen was heated at 50° C. for 30 minutes. The mixture was allowed to cool to ambient temperature and methanesulfonic acid 2-(1(3)-triphenylmethyl-4,5,6,7-tetrahydro-1H-benzimidazol-5-yl)ethyl ester (0.5 g, 1.2 mmol, prepared as described in Example 34) dissolved in dry DMF (5 ml) was added and the reaction mixture was stirred for 2 days. The mixture was poured into H2O (100 ml) and extracted with diethyl ether (2×50 ml). The combined organic extracts were washed with H2O (3×50 ml) and the solvent was evaporated. The residue was dissolved in 90% acetic acid (20 ml) and the mixture was heated at reflux for 1-2 hours. The volatiles were evaporated and the residue was stirred with a mixture of H2O (25 ml) and diethyl ether (20 ml). The phases were separated and the aqueous phase was washed with diethyl ether (2×20 ml). The aqueous phase was adjusted to pH 10-11 with 4 N sodium hydroxide and the oily precipitate was extracted with ethyl acetate (2×20 ml). The combined organic extracts were evaporated and the residue was dissolved in 1 N hydrochloric acid and re-evaporated. The residue was re-evaporated with acetone several times and then stirred with acetonitrile (5 ml). The mixture was filtered and the solid was discarded. The filtrate was evaporated to give 110 mg (31%) of the title compound.

1. temperatureto cool to ambient temperature
2. additionwas added
3. extractionextracted with diethyl ether (2×50 ml)
4. washThe combined organic extracts were washed with H2O (3×50 ml)
5. customthe solvent was evaporated
6. dissolutionThe residue was dissolved in 90% acetic acid (20 ml)
7. temperaturethe mixture was heated
8. temperatureat reflux for 1-2 hours
9. customThe volatiles were evaporated
10. stirringthe residue was stirred with a mixture of H2O (25 ml) and diethyl ether (20 ml)
11. customThe phases were separated
12. washthe aqueous phase was washed with diethyl ether (2×20 ml)
13. extractionthe oily precipitate was extracted with ethyl acetate (2×20 ml)
14. customThe combined organic extracts were evaporated
15. dissolutionthe residue was dissolved in 1 N hydrochloric acid
16. customre-evaporated
17. customThe residue was re-evaporated with acetone several times
18. stirringstirred with acetonitrile (5 ml)
19. filtrationThe mixture was filtered
20. customThe filtrate was evaporated

ORD record

ord-1bc0f1899d854a1fa70ca147e1f4215c

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610721B2