Piperazine → 1-Methyl-4-[2-(4-nitro-phenoxy)-ethyl]-piperazine

反応式

Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[C:20](#N)C.C(=O)([O-])[O-].[K+].[K+]>>[CH3:20][N:14]1[CH2:19][CH2:18][N:17]([CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)[CH2:16][CH2:15]1

参加物

反応物 4

HCID 4837Piperazine

HCID 6342Acetonitrile

HCID 11430Potassium Carbonate

HCID 2359871-(2-Bromoethoxy)-4-nitrobenzene

生成物 1

HCID 128308431-Methyl-4-[2-(4-nitro-phenoxy)-ethyl]-piperazine

反応条件

温度: 80 °C

実験手順

Into a 30 mL vial, 1-(2-Bromo-ethoxy)-4-nitro-benzene (5.00 g, 0.0203 mol), piperazine, 1-methyl-(4.51 mL, 0.0406 mol), Acetonitrile (15.0 mL, 0.287 mol) and Potassium carbonate (5.62 g, 0.0406 mol) were added. The reaction was heated at 80° C. for 4 hours. The reaction was partitioned with water and extracted with Et2O (3×100 mL). The Combined organic was washed with Brine, and dried over magnesium sulfate. The solid was filtered and washed with EtOAc. The solvent was removed under vacuum to afford 1-Methyl-4-[2-(4-nitro-phenoxy)-ethyl]-piperazine as an off white solid (3.89 g, 73%). NMR 1H (DSMO-d6-8.20 (dd, 2H, JJ=2.04, 5.12 Hz), 7.16 (dd, 2H, JJ=2.04, 5.08 Hz), 4.22 (t, 2H, J=5.76 Hz), 2.71 (t, 2H, J=5.72 Hz), 2.18-2.6 (bm, 8H), 2.13 (s, 3H)