Bicyclo(2.2.2)octane-1,4-diamine dihydrochloride → Bicyclo[2.2.2]octane-1,4-diamine

DOWEX® 550A-OH hydroxide resin (Aldrich, 75 g) was suspended in methanol, filtered, rinsed with methanol, and partially air dried. A portion of 1,4-diamino-bicyclo[2.2.2]octane dihydrochloride (10 g, 46.8 mmol) was taken up in methanol (200 mL), then treated with the above hydroxyl resin and stirred for 30 min (making sure all white clumps were dissolved). The mixture was filtered, the resin rinsed with methanol, and the filtrate concentrated in vacuo to afford 6.46 g (98%) of 1,4-diaminobicyclo[2.2.2]octane free base as a white solid (caution: compound readily carbonates in air and must be stored under nitrogen).

1. filtrationfiltered
2. washrinsed with methanol, and partially air
3. customdried
4. dissolutionwere dissolved)
5. filtrationThe mixture was filtered
6. washthe resin rinsed with methanol
7. concentrationthe filtrate concentrated in vacuo

ORD record

ord-11bffe3b867441eeb13100278ec6199b

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842707B2