Potassium Iodide → tert-Butyl 1-(2-methoxyethyl)piperidin-4-ylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Iodide	HCID 4875	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Bromoethyl methyl ether	HCID 80972	—
Reactant	4-(N-Boc-amino)piperidine	HCID 723833	—
Solvent	Water	HCID 962	—
Solvent	Acetonitrile	HCID 6342	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	tert-Butyl 1-(2-methoxyethyl)piperidin-4-ylcarbamate	HCID 53256198	77.4%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A stirred mixture of tert-butyl piperidin-4-ylcarbamate (1.1 g, 5.5 mmol), 1-bromo-2-methoxyethane (0.69 g, 5.0 mmol), potassium iodide (0.83 g, 5.0 mmol), K2CO3 (0.69 g, 5.0 mmol) and CH3CN (10 mL) was heated to 80° C. in a sealed vessel for 18 hours. After cooling to ambient temperature, the mixture was diluted with EtOAc (15 mL) and water (15 mL). The phases were separated, and the organic phase washed with water, brine, dried (Na2SO4), filtered, and concentrated. The product was obtained as a waxy solid (1.0 g, 77%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07723330B2
Source dataset	uspto-grants-2010_05
ORD ID	ord-ea326ba9d6804b999a43de72bf2aa306
Source note	uspto-grants-2010_05