Dimethylamine → Dimethyl-(3-nitrobenzyl)-amine

A solution of 3-nitrobenzyl bromide (10, 1.67 g, 7.73 mmol) and N,N-dimethylamine (4.25 mL, 2M in THF) in anhydrous THF (30 mL) was heated at 40° C. overnight. The reaction mixture was diluted with 1N HCl (30 mL, aq.), the aqueous layer separated, and extracted with EtOAc (30 mL). The pH of the aqueous layer was then adjusted to 9 using saturated Na2CO3 (aq.) and the aqueous layer was extracted with EtOAc (50 mL). The organic layer was washed with water (40 mL), brine (40 mL), and dried over Na2SO4. The solids were filtered and the filtrate was concentrated on a rotavap to give 11 (1.2 g).

1. customthe aqueous layer separated
2. extractionextracted with EtOAc (30 mL)
3. extractionthe aqueous layer was extracted with EtOAc (50 mL)
4. washThe organic layer was washed with water (40 mL), brine (40 mL)
5. dry with materialdried over Na2SO4
6. filtrationThe solids were filtered
7. concentrationthe filtrate was concentrated on a rotavap

ORD record

ord-c7988076d0cf49a78bf5a45bf0b280d9

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07265122B2