Potassium Carbonate → [3-(2-Morpholin-4-yl-ethylamino)-benzyl]-carbamic acid isopropyl ester

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	L-Proline	HCID 145742	—
Reactant	2-Morpholinoethylamine	HCID 408285	—
Reactant	tert-Butyl 3-iodobenzylcarbamate	HCID 11645663	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	[3-(2-Morpholin-4-yl-ethylamino)-benzyl]-carbamic acid isopropyl ester	HCID 67415913	76.3%

Reaction Conditions

Temperature	85 °C

Reaction Steps

A mixture of (3-iodo-benzyl)-carbamic acid tert-butyl ester (272 mg, 0.816 mmol), 4-(2-aminoethyl)morpholine (0.16 mL, 1.225 mmol), K2CO3 (232 mg, 1.679 mmol), CuI (19 mg, 0.10 mmol), L-proline (19 mg, 0.163 mmol) and DMSO (5 mL) was heated at 85° C. for 1 h. The reaction was cooled, poured onto water and the aqueous layer extracted with EtOAc (×3). The organic layers were combined and washed with water, brine and dried (Na2SO4). Chromatography (MeOH/EtOAc) afforded [3-(2-morpholin-4-yl-ethylamino)-benzyl]-carbamic acid isopropyl ester (200 mg) as an orange viscous oil. m/z (M+1) 336.16.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08044041B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-b1b0976911de4e949281075102bade76
Source note	uspto-grants-2011_10