Hydrochloric Acid → HCID 19073317, compound

Participants

Reaction Conditions

Reaction Steps

A steel autoclave is charged with 42.47 g (0.20 mol) of 4-n-butylamino-2,2,6,6-tetramethylpiperidine [EP-A-302 020, Example 1, page 4], 3 ml of concentrated hydrochloric acid and 300 ml of methanol. The autoclave is blanketed with nitrogen. 26.5 g (0.60 mol) of ethylene oxide are then introduced under pressure and the entire reaction mixture is heated to 150° C. The pressure in the autoclave is 10 bar. After 30 hours the reaction mixture is cooled to room temperature. About 250 ml of methanol are distilled off and the residue is poured into an aqueous saturated solution of sodium hydrogen carbonate and extracted three times with ethyl acetate. The organic phases are washed with an aqueous solution of saturated sodium chloride, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Chromatography of the residue over silica gel using the solvent system hexane/ethyl acetate 3:1 to 1:1 and ethyl acetate gives 31.5 g (53%) of 2-(n-butyl-[1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine-4-yl]amino)ethanol (compound (202)) in the form of a pale yellow oil.

Provenance & Evidence