Dimethylformamide → Aniline, p-isopropyl-N-methyl-

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Methylamine	HCID 6329	—
Reactant	1-Bromo-4-isopropylbenzene	HCID 11462	—
Reactant	Potassium Acetate	HCID 517044	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Water	HCID 962	—
Product	Aniline, p-isopropyl-N-methyl-	HCID 138880	34%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 1-bromo-4-isopropylbenzene (1.0 g, 5.03 mmol), methylamine (25 mL, 50.0 mmol), CuI (1.15 g, 6.0 mmol), KOAc (1.24 g, 12.6 mmol) and DMF (30 mL) in a sealed tube under N2 was heated to 100° C. overnight. The mixture was cooled to r.t., diluted with water (100 mL), and extracted with EtOAc. The organic layer was dried (Na2SO4), concentrated, and purified by silica gel chromatography (PE:EtOAc=10:1) to give 254 mg (34%) of the title compound as a yellow oil. [M+H] Calc'd for C10H15N, 150. Found, 150.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09242968B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-3e16f4e465e840d68cec29f74c2d0697
Source note	uspto-grants-2016_01