2-(Piperidin-4-yl)propane-1,3-diol hydrochloride synthesis

Yield:-

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane;methanol at 20; for 1 h;

Steps:

15

A mixture of 1-tert-butoxycarbonylpiperidine-4-ol, triethylamine, benzenesulfonyl chloride and methylene chloride was stirred for two days at room temperature to give 1-tert-butoxycarbonylpiperidine-4-ylbenzenesulfonate. A mixture of the obtained 1-tert-butoxycarbonylpiperidine-4-ylbenzenesulfonate, diethyl malonate, 20% sodium ethoxide-EtOH solution and EtOH was stirred for 22 hours heated to reflux to give diethyl [1-(tert-butoxycarbonyl)piperidine-4-yl]malonate. A mixture of the obtained diethyl [1-(tert-butoxycarbonyl) piperidine-4-yl]malonate, lithium borohydride, toluene and THF was stirred for 18 hours at 60°C to give 2-(1-tert-butoxycarbonyl piperidine-4-yl)propane-1,3-diol. A mixture of the obtained 2-(1-tert-butoxycarbonylpiperidine-4-yl)propane-1,3-diol, 4M HCl-dioxane solution and MeOH was stirred for one hour at room temperature to give 2-piperidine-4-ylpropane-1,3-diol hydrochloride. MS: 160

References:

EP1806347,2007,A1 Location in patent:Page/Page column 17