Potassium Carbonate → HCID 11716432, compound

Temperature

85 °C

To a suspension of 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.3055 g, 1.04 mmol) in 1,2-dichloroethane (17 mL) was added AlCl3 (0.6675 g, 5.04 mmol). The reaction was allowed to stir for 10 min and then TMSCN (0.68 mL, 5.10 mmol) was added. The reaction was sealed and heated to 85° C. for overnight. The reaction mixture was poured into a separatory funnel containing K2CO3 (aq. sat.) (100 mL) and EtOAc (100 mL). The aqueous phase was separated and further extracted with EtOAc (3×100 mL) was performed. The combined organics were dried over MgSO4, filtered and concentrated under vacuum. The residue was dissolved in DMSO and purified by Gilson preparatory HPLC (w/0.1% TFA). The combined fractions were concentrated down under vacuum to remove CH3CN. The resulting water layer was basified to pH=12 with 6N NaOH, and then extracted with EtOAc. The combined organic fractions were dried over MgSO4, filtered, and concentrated under vacuum to give the title compound (0.185 g, 59.7%). EI-MS ml/z 303 (M+H+) Rt (1.76 min).

1. customThe reaction was sealed
2. additionThe reaction mixture was poured into a separatory funnel
3. customThe aqueous phase was separated
4. extractionfurther extracted with EtOAc (3×100 mL)
5. dry with materialThe combined organics were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. dissolutionThe residue was dissolved in DMSO
9. custompurified by Gilson preparatory HPLC (w/0.1% TFA)
10. concentrationThe combined fractions were concentrated down under vacuum
11. customto remove CH3CN
12. extractionextracted with EtOAc
13. dry with materialThe combined organic fractions were dried over MgSO4
14. filtrationfiltered
15. concentrationconcentrated under vacuum

ORD record

ord-826fdc2d67a24f6095e9654074e137d1

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07598267B2