Water → 1-Benzyl-4-hydroxy-4-(1,4-benzodioxan-5-yl)piperidine

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	1-Benzyl-4-piperidone	HCID 19220	—
Reactant	5-Bromo-2,3-dihydro-1,4-benzodioxine	HCID 18787268	—
Reactant	Butyllithium	HCID 178418339	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Hexane	HCID 8058	—
Product	1-Benzyl-4-hydroxy-4-(1,4-benzodioxan-5-yl)piperidine	HCID 19082002	—

Reaction Conditions

Temperature	-60 °C

Reaction Steps

23.3 ml of a 1.6M solution of butyllithium in hexane are added dropwise to a solution, previously cooled to -60° C., of 8 g of 5-bromo-1,4-benzodioxane in 400 ml of tetrahydrofuran. When the addition is complete, the mixture is stirred at -60° C. for 5 minutes and a solution of 8 g of 1-benzylpiperid-4-one in 100 ml of tetrahydrofuran is then added dropwise. The mixture is stirred for 2 hours at -40° C. and then for 2 hours at ambient temperature before hydrolyzing using 80 ml of water.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05242933
Source dataset	uspto-grants-1993_09
ORD ID	ord-c53f731d9de94323887be2d52a3919fc
Source note	uspto-grants-1993_09