Hydrochloric Acid → HCID 86693072, compound

Into a 1000-mL round-bottom flask was placed 5-bromo-N-(2,2-dimethoxyethyl)-9-azatricyclo[8.1.1.0[2,7]]dodeca-2,4,6,8-tetraen-8-amine (33.4 g, 98.46 mmol, 1.00 equiv), tetrahydrofuran (340 mL), and hydrogen chloride (340 mL, 10%). The resulting solution was heated to reflux for 2 h, concentrated under vacuum and extracted with 2×150 mL of ethyl acetate. The pH value of the combined aqueous layers was adjusted to 8-9 with sodium hydroxide (2 mol/L). The resulting solution was extracted with 3×300 mL of dichloromethane. The organic layers were combined, washed with 2×150 mL of water and 1×150 mL of brine, dried over anhydrous sodium sulfated and concentrated under vacuum. The crude product was decolorized by the addition of active carbon, stirring for 30 min. The solids were filtered out and the filtrate was concentrated under vacuum to afford 15 g (55%) of 9-bromo-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7,9,11-pentaene as a white solid.

1. customInto a 1000-mL round-bottom flask was placed
2. temperatureThe resulting solution was heated
3. temperatureto reflux for 2 h
4. concentrationconcentrated under vacuum
5. extractionextracted with 2×150 mL of ethyl acetate
6. extractionThe resulting solution was extracted with 3×300 mL of dichloromethane
7. washwashed with 2×150 mL of water and 1×150 mL of brine
8. dry with materialdried over anhydrous sodium
9. concentrationconcentrated under vacuum
10. additionThe crude product was decolorized by the addition of active carbon
11. filtrationThe solids were filtered out
12. concentrationthe filtrate was concentrated under vacuum

ORD record

ord-7dadd9b58bc245bea9de99da06acd882

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034866B2