Sodium Bicarbonate → HCID 22236594, compound

Temperature

0 °C

To a solution of 4-methyl-1,2,3,4,5,6-hexahydro-benzo[e][1,4]diazocine (1.2 g, 6.8 mmole) in hydrochloric acid (2 N, 30 mL) cooled to 0° C. was added sodium nitrite (0.9 g, 13 mmole) in water (5 mL). The mixture was stirred for 1 hour at 0° C. and then neutralized with solid sodium bicarbonate and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with saturated aqueous sodium chloride (200 mL), dried and concentrated to a light brown oil. This oil was redissolved in THF (50 mL) and added to a suspension of lithium aluminum hydride (1.0 g, 25 mmole) in THF (50 mL) and the mixture refluxed for 3 hours under nitrogen. The excess hydride was destroyed at 0° C. by the cautious addition of water. The mixture was diluted with THF (200 mL) and filtered. Evaporation of the filtrate in vacuo provided 1.4 g of the title compound as a light yellow oil.

1. extractionextracted with ethyl acetate (3×100 mL)
2. washThe combined organic layers were washed with saturated aqueous sodium chloride (200 mL)
3. customdried
4. concentrationconcentrated to a light brown oil
5. dissolutionThis oil was redissolved in THF (50 mL)
6. temperaturethe mixture refluxed for 3 hours under nitrogen
7. customThe excess hydride was destroyed at 0° C. by the cautious addition of water
8. additionThe mixture was diluted with THF (200 mL)
9. filtrationfiltered
10. customEvaporation of the filtrate in vacuo

ORD record

ord-68d00760179c47e88b05696e01b9d834

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07012089B2