1-Pyrrolidineethanamine → 4-[3-(2-Pyrrolidin-1-yl-ethylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	1-Pyrrolidineethanamine	HCID 1344	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	tert-Butyl 4-(3-bromophenyl)piperazine-1-carboxylate	HCID 10882380	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	4-[3-(2-Pyrrolidin-1-yl-ethylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester	HCID 67415909	62%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 4-(3-bromo-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (300 mg, 0.88 mmol), 2-pyrrolidin-1-yl-ethylamine (0.165 mL, 1.32 mmol), Pd2(dba)3 (40 mg, 0.044 mmol), xantphos (50 mg, 0.088 mmol) and NaOt-Bu (124 mg, 1.32 mmol) in dioxane (15 mL) was bubbled with nitrogen in a sealed tube for 10 min. The mixture was heated at 120° C. for 2 h. After this time the mixture was cooled and filtered through celite and concentrated. Chromatography on silica (ethyl acetate/MeOH) provided the title compound (203 mg, 62%). m/z (M+1) 375.53

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08044041B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-117f98538b0344118046f47b1fbc7413
Source note	uspto-grants-2011_10