N-Methylaniline → N-(3-bromopropyl)-N-methylaniline

Temperature

35 °C

N-methylaniline (300 mg, 2.80 mmol), 1,3-dibromopropane (0.568 mL, 5.6 mmol), K2CO3 (1.16 g, 8.40 mmol) and 18-crown-6 (49.8 mg, 0.30 mmol) were dissolved in 20 mL of anhydrous DMF and mixture stirred for 24 hours at 35° C. The reaction mixture was filtered and washed with DCM, and filtrate dissolved in DCM (100 mL) before extraction in water. The organic layer was washed with water (2×50 ml), brine (50 ml), and dried over Na2SO4, followed by evaporation of solvents under reduced pressure and the residue purified by silica gel column chromatography (EtOAc:n-hexane 1:20 to 1:10) to obtain compound 14. Yield: 0.260 g (74%). 1H NMR (500 MHz, CDCl3): δ 2.16 (tt, 2H, J=6.5 and 13.5 Hz, Hc), 2.99 (s, 3H, NCH3, Ha), 3.46-3.55 (m, 4H, Hb and Hd), 6.71-6.79 (m, 2H, He and Hg), 7.24-7.29 (m, 2H, Hf). EI-MS: [M+H]+ C10H15BrN calcd 228.03, obsd 228.04.

1. filtrationThe reaction mixture was filtered
2. washwashed with DCM, and filtrate
3. dissolutiondissolved in DCM (100 mL) before extraction in water
4. washThe organic layer was washed with water (2×50 ml), brine (50 ml)
5. dry with materialdried over Na2SO4
6. customfollowed by evaporation of solvents under reduced pressure
7. customthe residue purified by silica gel column chromatography (EtOAc:n-hexane 1:20 to 1:10)

ORD record

ord-cbff44278474417ba89161a4a382791e

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09345781B2