[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.B(Cl)(Cl)Cl.[C:18]1([CH:28]=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.[OH-].[Na+]>C1C=CC=CC=1.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([CH:28]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[OH:29])[CH:3]=1
A solution of (4-chloro-phenyl)-(neopentyl)-amine (6.58 g, 33.3 mmol) in benzene (15 mL) was added to a solution of boron trichloride (1.0 M in xylenes; 36.6 mL, 36.6 mmol) in benzene (40 mL) at 0° C. under a nitrogen atmosphere. Once the addition was complete, the resulting mixture was heated at reflux for 2 hours and then recooled to 0° C. A solution of 1-naphthaldehyde (5.72 g, 36.6 mmol, 5.0 mL), triethylamine (6.74 g, 66.6 mmol, 9.3 mL) and benzene (15 mL) was then added and the resulting mixture stirred 1 hour before diluting with ethyl acetate and aqueous 2N hydrochloric acid. The resulting mixture was shaken vigorously, the aqueous layer alkalized with aqueous 5N sodium hydroxide, and the layers separated. The aqueous layer was extracted with ethyl acetate (2×). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by flash column chromatography (5:1 hexanes/ethyl acetate) to produce 7.95 g (67%) of the title compound as a pale yellow solid.
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