1H,2H,3H,4H,5H,6H-azepino(4,5-b)indole → HCID 59075496, compound

A solution of 1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.93 g, 5.0 mmol) in trifluoroacetic acid (17 mL) was cooled to 0° C., and treated with a freshly prepared solution of Na(CN)BH3 (1.57 g, 25 mmol) in MeOH (4 mL). The cooling bath was removed and the reaction mixture was stirred at room temperature for 1 h, then treated with water (75 mL), stirred for an additional 15 minutes before adjusting the pH to 14 with 45% KOH (aqueous). The resulting solution was extracted with EtOAc (3×40 mL), and the combined organic extracts were washed once with brine, dried over MgSO4, filtered, and concentrated in vacuo to give a yellow syrup. The crude product was purified by chromatography and using ethanol:ammonia:dichloromethane (15:1.5:83.5) and trituration of the resulting material gave the title compound (0.64 g) as an off-white solid: mp 102-114° C.

1. customThe cooling bath was removed
2. additiontreated with water (75 mL)
3. stirringstirred for an additional 15 minutes
4. extractionThe resulting solution was extracted with EtOAc (3×40 mL)
5. washthe combined organic extracts were washed once with brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give a yellow syrup
10. customThe crude product was purified by chromatography

ORD record

ord-0ee4e68ba74d4f64936c7189c06d7255

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06586421B2