Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1.C(#N)C.C(=O)([O-])[O-].[K+].[K+].[CH3:22][C:23]1([CH3:29])[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]1>[I-].[K+].CCCCCCC>[I:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:25]2[CH2:26][CH2:27][CH2:28][C:23]([CH3:29])([CH3:22])[CH2:24]2)=[CH:7][CH:8]=1
A mixture of 1-[(3-chloropropyl)oxy]-4-iodobenzene (100 g) and acetonitrile (600 ml) is stirred for about 5 min at 25-35° C., then potassium carbonate (93.07 g) followed by 3,3-dimethylpiperidine (49.53 g) are added over about 10 min. Potassium iodide (2.24 g) is added, then the mixture is stirred for about 15 min, before being heated to 78-82° C. for 22-24 h. The reaction mixture is cooled to 25-35° C., and the solid residue is filtered and washed with acetonitrile (200 ml). The filtrate and washings are concentrated under reduced pressure at 50-60° C. to give a thick liquid which is stirred with n-heptane (100 ml) for about 30 min at 25-30° C. The solution is then cooled to −5 to 10° C. and stirred for about 30 min. The solid is filtered, washed with chilled n-heptane (50 ml, 0-5° C.), then dried at 35-40° C. under vacuum for 6-10 h to give the title compound (97 g).
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