1,4-Dioxane hydrochloride → 2-(Piperidin-4-YL)propane-1,3-diol hydrochloride

HRID 225473Notes

Reaction equation

HRID 225473 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([CH2:17][OH:18])[CH2:15][OH:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:19].O1CCOCC1>CO>[ClH:19].[NH:8]1[CH2:13][CH2:12][CH:11]([CH:14]([CH2:17][OH:18])[CH2:15][OH:16])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59605609Tert-butyl 4-(1,3-dihydroxypropan-2-yl)piperidine-1-carboxylate

Product 1

HCID 671972312-(Piperidin-4-YL)propane-1,3-diol hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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-butoxycarbonylpiperidine-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.

Sources & evidence

ORD record
ord-5a24eae633374f0a94ef399cf9c6e8b2
Source dataset
uspto-grants-2009_07
Patent number
US07557112B2

Reaction notes

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