[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C[O-].[Na+].[C:27](OC(=O)C)(=[O:29])C.O>CO.C(Cl)Cl>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:29][CH3:27])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]A solution of crude 1-acetyl-4-[4-(6-bromohexyloxy)phenyl]piperazine (10.52 g) in methanol (105 ml) was treated with 28% sodium methoxide in methanol (105 ml), and the solution was refluxed for 7 hours. After cooling, the precipitate was removed by filtration. The filtrate was added to a mixture of methylene chloride and water. The organic layer was taken, dried over magnesium sulfate, filtered and evaporated to give a crude oil. This oil in methylene chloride (20 ml) was treated with acetic anhydride (6.4 ml) under ice-cooling. After 6 hours, the solution was added to a mixture of methylene chloride and water. The organic layer was taken, dried over magnesium sulfate, filtered and evaporated. The residue was purified by silica gel column chromatography eluting with a mixed solvent of methylene chloride-methanol (from 0% to 3% gradient elution) to give 1-acetyl-4-[4-(6-methoxyhexyloxy)phenyl]piperazine (5.38 g) as a pale red solid.
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