Cyclopropylamine → 2-(4-Bromo-phenyl)-N-cyclopropyl-propionamide

Participants

Role	Name	HCID	Charge
Reactant	Cyclopropylamine	HCID 69828	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-(4-Bromophenyl)propanoic acid	HCID 521441	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(4-Bromo-phenyl)-N-cyclopropyl-propionamide	HCID 84356328	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a mixture of 18.0 g (79.0 mmol) 2-(4-bromo-phenyl)-propionic acid (Bioorg. Med. Chem. Lett. 2010, 20, 887) and 68.4 mL (393 mmol) DIPEA in 90 mL DMF, 50.5 g (157 mmol) TBTU are added. The mixture is stirred for 15 min at 0° C. After that time, 16.3 mL (236 mmol) cyclopropylamine are added and the mixture is stirred for 16 h at rt. After that time, iced water is added and the mixture is extracted with EtOAc. The organic layer is washed with brine and dried over sodium sulphate. The solvent is evaporated and the residue is purified by column chromatography (silica gel; hexane/EtOAc 7:3) to yield the desired product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08759528B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-40014c6d3dcb40f78be0041792940b3b
Source note	uspto-grants-2014_06