Potassium Carbonate → tert-Butyl (1-(pyridin-4-yl)piperidin-4-yl)methylcarbamate

https://huagongshe.com/reaction/1193302

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Bromopyridine	HCID 14268	—
Reactant	L-Proline	HCID 145742	—
Reactant	Tert-butyl (piperidin-4-ylmethyl)carbamate	HCID 723429	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Sodium Chloride	HCID 5234	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	tert-Butyl (1-(pyridin-4-yl)piperidin-4-yl)methylcarbamate	HCID 20801237	30%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Potassium carbonate (3 eq), L-proline (0.4 eq), CuI (0.2 eq) and 4-bromopyridine (1 eq) were added under a protecting gas atmosphere to a solution of tert-butyl piperidin-4-ylmethyl-carbamate (3 g, 15 mmol) in DMSO. The reaction mixture was heated for 20 h at 100° C. After cooling to room temperature, the mixture was diluted with ethyl acetate and sat. sodium chloride solution and filtered over Celite, and the residue was then washed with ethyl acetate. The phases were separated, dried and concentrated under reduced pressure. The crude product was purified by column chromatography. Yield: 30%

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08680159B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-665ac254d1b84f6db03f0d61f23a579b
Source note	uspto-grants-2014_03