Hydrochloric Acid → HCID 44210009, compound

(±) 3-(α-Bromoacetyl)-1-azabicyclo [2.2.2 ]octane hydrobromide (EP-0366304, Description 7) (1.0 g, 3.2 mmol) was converted into (±) 2-oxo-2-(1-azabicyclo[2.2.2]octan-3-yl)ethanal hydrobromide using the method described in Example 3. The crude aldehyde was immediately treated with a suspension of aminoguanidine bicarbonate (0.48 g, 3.5 mmol) in water (10 ml), and the solution was acidified to pH4 with 5M hydrochloric acid. The reaction mixture was stirred overnight at room temperature then heated under reflux for 1 h. It was then saturated with potassium carbonate and extracted into chloroform (4×10 ml). The combined organic extracts were dried over sodium sulphate, concentrated in vacuo and the residue chromatographed on neutral alumina in a gradient of 0-8% methanol in chloroform. This afforded the title compound (E6) as a colourless solid (42 mg, 6%) which was converted into the oxalate salt m.p. 175° C. (dec) (from methanol - ether).

1. temperaturethen heated
2. temperatureunder reflux for 1 h
3. extractionsaturated with potassium carbonate and extracted into chloroform (4×10 ml)
4. dry with materialThe combined organic extracts were dried over sodium sulphate
5. concentrationconcentrated in vacuo
6. customthe residue chromatographed on neutral alumina in a gradient of 0-8% methanol in chloroform

ORD record

ord-901ae23fa3154159b99e8d5a82bc6e42

Source dataset

uspto-grants-1994_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05324724