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

To N-(4-Bromo-2-nitro-phenyl)-N,N′,N′-trimethyl-propane-1,3-diamine (Example 619, 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 기록

ord-0003bf079656431baa5fc2cabd301833

출처 데이터셋

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08476434B2