Dimethylamine → 4-{n-[2-Hydroxy-3-(n,n-dimethylamino)propyl]-n-methylamino}nitrobenzene

Temperature

0 °C

4-Nitro-N-methylaniline (1.00 g, 6.6 mmol) was dissolved in DMF (50 ml) and cooled to 0° C. in an ice bath. Sodium hydride (290 mg, 7.2 mmol, 60% dispersion in mineral oil) was added portion wise over 30 mins to give an orange/brown solution. To this was added epibromohydrin (0.62 ml, 7.2 mmol) dropwise and the mixture left to stir at ambient temperature for 12 hours. The mixture was evaporated to give a yellow oily residue, to which was added dimethylamine 2.0 M in MeOH (66 ml, 0.13 mol) and left to stir at ambient temperature for 12 hours. The mixture was evaporated to give a yellow solid, then taken up in DCM (100 ml), washed with H2O (20 ml), brine (20 ml), dried over MgSO4 and evaporated to dryness to give the title product as an orange solid (1.44 g, 86%). NMR (300 MHz): 2.2 (s, 6H), 2.3 (t, 2H), 3.1 (s, 3H), 3.3–3.6 (m, 2H), 3.8 (br s, 1H), 4.8 (d, 1H) 6.8 (d, 2H), 8.0 (d, 2H); m/z: (ES+) 254.0 (MH+).

1. customto give an orange/brown solution
2. waitthe mixture left
3. customThe mixture was evaporated
4. customto give a yellow oily residue
5. waitleft
6. stirringto stir at ambient temperature for 12 hours
7. customThe mixture was evaporated
8. customto give a yellow solid
9. washwashed with H2O (20 ml), brine (20 ml)
10. dry with materialdried over MgSO4
11. customevaporated to dryness

ORD record

ord-508c853561a245d4af4c721ce639755f

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07176212B2