Ethyl Acetate → 4-bromo-N1-(3-(dimethylamino)propyl)-N1-methylbenzene-1,2-diamine

Temperatur

80 °C

To N-(4-Bromo-2-nitro-phenyl)-N,N′,N′-trimethyl-propane-1,3-diamine (made by a method similar to that of Example 103-Step 1) (0.54 g, 1.7 mmol) in 20 ml EtOH was added SnCl2 (0.51 g, 2.67 mmol). The mixture was sealed and was heated to 80° C. for 12 h. An additional amount of SnCl2 (0.51 g, 2.67 mmol) was added and heating continued for 12 h. The reaction was cooled to ambient temperature, and was poured into a mixture of EtOAc and saturated aqueous sodium bicarbonate. The mixture was filtered through celite, and the organic layer was removed. The aqueous layer was extracted twice with EtOAc, and the combined organic layers were dried with Na2SO4, filtered, and concentrated to give a cloudy oil. This material was filtered through silica gel with 90/10/1 dichloromethane/MeOH/conc. NH4OH and concentrated in vacuo to give the title compound as a red oil. MS (ES+): 285.9 (M+H)+. Calc'd for C12H20BrN3: 286.21.

1. customThe mixture was sealed
2. temperatureheating
3. temperatureThe reaction was cooled to ambient temperature
4. filtrationThe mixture was filtered through celite
5. customthe organic layer was removed
6. extractionThe aqueous layer was extracted twice with EtOAc
7. dry with materialthe combined organic layers were dried with Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customto give a cloudy oil
11. filtrationThis material was filtered through silica gel with 90/10/1 dichloromethane/MeOH/conc
12. concentrationNH4OH and concentrated in vacuo

ORD-Eintrag

ord-8a7f7932cb434448b2d4dba82df15cda

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08557996B2