反応 #1592136

反応方程式

compound 27

methyl 4-(4-aminophenyl)butanoate

Ethylenediamine

AlMe3

water

→

compound 55

収率 96.0%

4-(3-(4,5-dihydro-1H-imidazol-2-yl)propyl)aniline

収率 96.0%

溶媒

Toluene

CH3OH

DCM

反応条件

後処理

1. 1
   その他did not exceed −20° C
2. 2
   workup.STIRRINGThe reaction mixture was stirred at 120° C. for overnight
3. 3
   温度After cooling
4. 4
   ろ過filtered with over MgSO4
5. 5
   濃縮The filtrate was concentrated
6. 6
   その他purified with silica gel column chromatography (EtOAc:CH3OH:TEA=3:1:0.2)

実験手順

Ethylenediamine (6.23 mL, 93.1 mmol) was added dropwise to a stirred solution of AlMe3/Tol (58 mL, 2M), so that the temperature did not exceed −20° C. The reaction mixture was stirred at room temperature for 10 min, then to the mixture was added dropwise a solution of the compound 27 (4.5 g, 23.3 mmol) in Toluene (290 mL). The reaction mixture was stirred at 120° C. for overnight. After cooling, the solution was treated dropwise with water, diluted DCM and CH3OH and filtered with over MgSO4. The filtrate was concentrated and purified with silica gel column chromatography (EtOAc:CH3OH:TEA=3:1:0.2) to give the compound 55 (4.5 g, 96%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ6.96 (d, 2H, J=8.3 Hz), 6.62 (d, 2H, J=8.3 Hz), 3.56 (s, 4H), 2.55 (t, 2H, J=7.4 Hz), 2.23 (d, 2H, J=7.4 Hz), 1.84-1.94 (m, 2H).

出典