Sodium Chloride → HCID 14022405, compound

N-Acetyl-4-(2,2-diethoxyethoxy)piperidine (12 g.) in 0.5 N hydrochloric acid (50 ml.) was stirred at room temperature overnight. The solution was saturated with sodium chloride and extracted several times with chloroform (total 500 mls.). The chloroform extract was dried (Na2SO4) and the solvent evaporated in vacuo and with a bath temperature below 30° C. The resultant intermediate aldehyde (9.8 g.) was reduced immediately with sodium borohydride (0.75 g.) in ethanol (75 ml.), at pH 6. After stirring for 3 hours at room temperature reduction was complete. Water was then added to the stirred solution and the organic solvent evaporated in vacuo. The residue was taken up in water (30 ml.), extracted with chloroform (10×30 ml.), the combined chloroform extracts dried (Na2SO4) and the solvent evaporated in vacuo. The residue was taken up in water (70 ml.) and washed with petroleum ether (2×10 ml.). The aqueous phase was concentrated to give N-acetyl-4-(2-hydroxyethoxy)piperidine (6.9 g.) characterized spectroscopically. A sample was distilled and had a b.p. of 139°-140° C./0.3 mm.

1. extractionextracted several times with chloroform (total 500 mls.)
2. extractionThe chloroform extract
3. dry with materialwas dried (Na2SO4)
4. customthe solvent evaporated in vacuo and with a bath temperature below 30° C
5. additionWater was then added to the stirred solution
6. customthe organic solvent evaporated in vacuo
7. extractionextracted with chloroform (10×30 ml.)
8. dry with materialthe combined chloroform extracts dried (Na2SO4)
9. customthe solvent evaporated in vacuo
10. washwashed with petroleum ether (2×10 ml.)
11. concentrationThe aqueous phase was concentrated

ORD record

ord-f02ba4c0f1ec4733be7b7c919efee2d0

Source dataset

uspto-grants-1980_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04237138