Potassium Carbonate → HCID 19610919, compound

3-Quinuclidinyl-hydrazine (D2) (5.0 g, 35.5 mmol) was added to a solution of K2CO3 (4.90 g, 35.5 mmol) in water (13 ml) and the ice-cooled solution was stirred vigorously while 2-chloroacrylonitrile (3.10 g, 2.83 ml, 35.5 mmol) was added dropwise over 1 minute. The solution was then stirred at room temperature overnight. The mixture was diluted with MeOH, evaporated to a slurry under reduced pressure, suspended in saturated aqueous potassium carbonate and extracted with EtOAc (3×100 ml), followed by CHCl3 (4×250 ml). The organic extracts were dried (Na2SO4), filtered and evaporated to dryness under reduced pressure to yield a brown oil, which was purified by column chromatography (neutral alumina eluting with chloroform), to yield a faster running fraction (E3) (44 mg) and a slower running fraction (E4) (32 mg). Both were crystallised separately by trituration with diethyl ether, to yield white crystalline solids.

1. additionwas added dropwise over 1 minute
2. customevaporated to a slurry under reduced pressure
3. extractionextracted with EtOAc (3×100 ml)
4. dry with materialThe organic extracts were dried (Na2SO4)
5. filtrationfiltered
6. customevaporated to dryness under reduced pressure
7. customto yield a brown oil, which
8. customwas purified by column chromatography (neutral alumina eluting with chloroform)
9. customto yield
10. customBoth were crystallised separately by trituration with diethyl ether
11. customto yield white crystalline solids

ORD record

ord-8e25786e6f384d7fbf27f0a3a0a249cc

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05981545