p-Fluoronitrobenzene → 4-Nitrophenyl-cis-2,5-dimethylpiperazine

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F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][C@H:12]1[CH2:17][NH:16][C@@H:15]([CH3:18])[CH2:14][NH:13]1.C(=O)(O)[O-].[Na+]>C(O)CCCC>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:13]2[CH2:14][C@H:15]([CH3:18])[NH:16][CH2:17][C@@H:12]2[CH3:11])=[CH:3][CH:4]=1)([O-:10])=[O:9]

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실험 절차

A mixture of 4-fluoronitrobenzene (30.34 g, 0.22 mole), cis-2,5-dimethylpiperazine (25 g, 0.22 mole) and sodium bicarbonate (24 g, 0.28 mole) in n-pentanol (150 ml) was heated under nitrogen at 90°-100° for 18 hours. After filtration, the n-pentanol was removed under reduced pressure and the residue was partitioned between methylene chloride and water. The organic phase was separated, washed again with water, dried over magnesium sulphate, and concentrated under reduced pressure. The residue was triturated with ice water to yield a yellow solid. The solid was filtered off and dried to yield the title compound, m.p. 93°-4° (37 g, 71%).