반응 #830877
ord-0e1de8cc8f204e0886746758177ba9b7
반응 방정식
반응 조건
후처리
- 1온도was heated
- 2온도at reflux for 60 h
- 3온도the mixture heated
- 4온도at reflux for a further 18 h
- 5온도The mixture was cooled to 0° C.
- 6여과filtered
- 7기타The solid was collected
- 8세척washed with anhydrous ether
- 9기타then partitioned between dichloromethane (200 ml) and sodium hydroxide solution (1M, 150 ml)
- 10기타The organic layer was separated
- 11세척the aqueous phase washed once more with dichloromethane (200 ml)
- 12건조The combined organic layers were dried (K2CO3)
- 13기타evaporated in vacuo
- 14기타The resultant residue was chromatographed on silica gel
- 15기타to afford an orange oil
- 16기타The oil crystallized
- 17기타the resultant solid was triturated with petrol (60/80)
실험 절차
A mixture of N-methylbis(2-chloroethyl)-amine hydrochloride (9.8 g) and 3-nitroaniline (7.0 g) in 1-butanol (100 ml) was heated at reflux for 60 h then cooled to room temperature. Sodium carbonate (2.8 g) was added and the mixture heated at reflux for a further 18 h. The mixture was cooled to 0° C. and filtered. The solid was collected, washed with anhydrous ether then partitioned between dichloromethane (200 ml) and sodium hydroxide solution (1M, 150 ml). The organic layer was separated and the aqueous phase washed once more with dichloromethane (200 ml). The combined organic layers were dried (K2CO3) and evaporated in vacuo. The resultant residue was chromatographed on silica gel, using dichloromethane:methanol (96:4) as the eluant, to afford an orange oil. The oil crystallized on standing and the resultant solid was triturated with petrol (60/80) to give the desired piperazine (5.64 g). 1H NMR (360 MHz, CDCl3) δ 2.37 (3H, s), 2.58 (4H, t, J=5 Hz), 3.30 (4H, t, J=5 Hz), 7.18 (1H, dd, J=9 and 3 Hz), 7.35 (1H, t, J=8 Hz), 7.64 (1H, dd, J=9 and 2 Hz), 7.71 (1H, d, J=2 Hz). MS (CI, NH3) 222 (M+1).