Hydrochloric Acid → HCID 88140050, compound

A mixture of E-(R)-1-(2-(((1-phenyl-1-octanylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester (0.3 g, 0.75 mmol, prepared as described in example 3), ethanol (5 ml) and 12N sodium hydroxide (0.27 ml) was stirred at ambient temperature for 2 h, then neutralised with 4N hydrochloric acid and concentrated to dryness in vacuo. The residue was dissolved in ethyl acetate (70 ml) and washed with water (20 ml). The aqueous phase was extracted with ethyl acetate (50 ml), the combined organic phases were washed with brine and dried (Na2SO4). The solvent was evaporated in vacuo and the residue dissolved in toluene (3 ml). The mixture was heated to 40° C. and then added to a freshly prepared solution of chloro trimethylsilane (40 μl) and methanol (4 μl) in toluene (0.14 ml). The mixture was allowed to cool to room temperature and the solvent was evaporated in vacuo. This afforded 0.13 g of the title compound as an oil. 1H-NMR (DMSO-d6) δ 4.32 (m,2H).

1. concentrationconcentrated to dryness in vacuo
2. dissolutionThe residue was dissolved in ethyl acetate (70 ml)
3. washwashed with water (20 ml)
4. extractionThe aqueous phase was extracted with ethyl acetate (50 ml)
5. washthe combined organic phases were washed with brine
6. dry with materialdried (Na2SO4)
7. customThe solvent was evaporated in vacuo
8. dissolutionthe residue dissolved in toluene (3 ml)
9. temperatureThe mixture was heated to 40° C.
10. additionadded to a freshly prepared solution of chloro trimethylsilane (40 μl) and methanol (4 μl) in toluene (0.14 ml)
11. temperatureto cool to room temperature
12. customthe solvent was evaporated in vacuo

ORD record

ord-7a2839e042b04c948b51460da645c2c5

Source dataset

uspto-grants-1997_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05608069