Pyridine → 4-Piperidinopiperidine-1-carbonyl chloride

Participants

Role	Name	HCID	Charge
Reactant	Pyridine	HCID 1049	—
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Dichloromethane	HCID 6344	—
Reactant	(19S)-5,19-diethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),4,6,9,15(20)-hexaene-8,14,18-trione	HCID 178436639	—
Solvent	Triethylamine	HCID 8471	—
Product	4-Piperidinopiperidine-1-carbonyl chloride	HCID 9813375	—

Reaction Conditions

Temperature	35 °C

Reaction Steps

In a suitable vessel were charged 7-Ethyl-10-hydroxycamptothecin (1 g), methylene dichloride, dimethylformamide (0.186 gm) and pyridine (3 ml) under nitrogen atmosphere. A solution of [1,4′]bipiperidinyl-1′-carbonyl chloride (0.88 g), methylene dichloride and triethylamine (1 ml) was prepared and added to the above suspension and stirred at 30-40° C. for 2 hours. The solvent was distilled out under reduced pressure at 50° C. and hexane was added under stirring as an antisolvent to isolate crystalline compound, which was then filtered, washed with hexane and dried under reduced pressure at 50° C. The yield was 1.30 g (86.89%); HPLC purity—99.8%

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546573B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-dad8ff0cac2948c4b0cd6eb100d618d6
Source note	uspto-grants-2013_10