Dimethylamine → n,n-Dimethyl-2-(4-nitrophenyl)ethanamine

A pressure tube was charged with 1-(2-bromoethyl)-4-nitrobenzene (1 g, 4.35 mmol) in acetonitrile (5 mL). Triethylamine (2.4 mL) and dimethylamine, 2M in tetrahydrofuran (0.784 g, 17.39 mmol) were added, and the sealed tube was stirred at ambient temperature for 2 days. The reaction mixture was partitioned between dilute NaHCO3 solution and ethyl acetate, then extracted another two times with ethyl acetate. The product was then extracted into 2N HCl (2×25 mL). Following neutralization with 2N NaOH, the aqueous mixture was extracted with ethyl acetate (3×). The extracts were dried (Na2SO4), filtered and concentrated to give the title compound. MS (ESI(+)) m/e 194.9 (M+H)+.

1. customThe reaction mixture was partitioned between dilute NaHCO3 solution and ethyl acetate
2. extractionextracted another two times with ethyl acetate
3. extractionThe product was then extracted into 2N HCl (2×25 mL)
4. extractionthe aqueous mixture was extracted with ethyl acetate (3×)
5. dry with materialThe extracts were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated

ORD-Eintrag

ord-cd3e9be9e3054569bbbfb06b5a17910c

Quelldatensatz

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08354422B2