Dabco → HCID 19383076, compound

To a stirred solution of 1,4-diazabicyclo[2.2.2]octane (17.93 g, 0.1599 mol) in 200 ml of acetonitrile at 0° C. was added dropwise a solution of 2-bromoacetamide (20.05 g, 0.1453 mol) in 200 ml of acetonitrile during 25 min. A precipitate began depositing several minutes into the addition. The milky-white reaction mixture was stirred and allowed to warm to room temperature overnight. After 20 h, the white solid was isolated by filtration, washing with ~200 ml of acetonitrile. Drying in vacuo gave 33.37 g of white solid. This material was combined with product from a previous preparation giving a total of 37.93 g for recrystallization. The solid was dissolved in ~230 ml of boiling ethanol, filtered while hot, and allowed to cool slowly overnight. The solution was seeded while still very warm. The mother liquors were decanted from the dense crystalline mass and the crystals were washed three times with cold ethanol (~50 ml total). Drying in vacuo gave 30.47 g of 1 as large colorless hygroscopic prisms, mp 194°-198° C.

1. additionA precipitate began depositing several minutes into the addition
2. customthe white solid was isolated by filtration
3. washwashing with ~200 ml of acetonitrile
4. customDrying in vacuo

ORD record

ord-a6473b532cc440a080ad72200af1059d

Source dataset

uspto-grants-1995_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05451579