Benzylamine → 4-(4-Benzylamino-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Benzylamine	HCID 7504	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	Tert-butyl 4-(4-bromophenyl)-3,6-dihydropyridine-1(2h)-carboxylate	HCID 54371851	—
Catalyst	Binap, (A+-)-	HCID 634876	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	4-(4-Benzylamino-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester	HCID 53748737	73.7%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a solution of 4-(4-bromo-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.34 g), benzylamine (0.12 g) and sodium tert-butoxide (0.13 g) in toluene (8 mL) were added tris(dibenzylidene acetone)dipalladium (2.2 mg) and Binap (4.6 mg) and the mixture was heated at 80° C. for 16 hours. The solution was then cooled to room temperature, filtered and the filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography eluting with petroleum ether/AcOEt (90/10) and the oily residue was crystallized from diisopropyl ether to give the title compound (0.27 g) as white crystals.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06552022B1
Source dataset	uspto-grants-2003_04
ORD ID	ord-9c1ca8c990864d51a54fac36ad021f03
Source note	uspto-grants-2003_04