Benzoyl chloride → [3-(3,4-Dichlorophenyl)-3-(3-hydroxy-propyl)-piperidin-1-yl]-phenyl-methanone

Participants

Role	Name	HCID	Charge
Reactant	Benzoyl chloride	HCID 7412	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	(R)-3-[3-(3,4-Dichlorophenyl)-piperidin-3-yl]-propan-1-ol(1s)-7,7-dimethyl-2-oxobicyclo[2,2,1]heptane-1-methanesulfonate	HCID 131724007	—
Solvent	Dichloromethane	HCID 6344	—
Product	[3-(3,4-Dichlorophenyl)-3-(3-hydroxy-propyl)-piperidin-1-yl]-phenyl-methanone	HCID 22741724	89.8%

Reaction Steps

Diisopropylethylamine(5.7 mL, 3.27 mmol, 5.0 eq) was added to a mixture of camphorsulfonate salt (9) (3.4 g, 6.53 mmol) in CH2Cl2 (21 mL, 0.3 M) and followed by dropwise addition of PhCOCl (0.83 mL, 7.19 mmol, 1.1 eq). The solution was stirred at room temperature for 1 hour. The reacting mixture was diluted with CH2Cl2 (200 mL) and washed with brine, 1 M KHSO4, and saturated NaHCO3 then dried over MgSO4. The concentrated crude oil was purified by flash chromatography (CH2Cl2-MeOH/95:5) to give white solid (2.30 g, 89.8%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06602886B2
Source dataset	uspto-grants-2003_08
ORD ID	ord-ebda47b7e3ba4ce1b5ae61b0d6bbbf8d
Source note	uspto-grants-2003_08