[K].CC(O)(C)C.[CH2:7]([N:14]([CH2:23][CH2:24][CH2:25][C:26]([O:28]CC)=O)[CH2:15][CH2:16][CH2:17]C(OCC)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C1(C)C(C)=CC=CC=1>[CH2:7]([N:14]1[CH2:15][CH2:16][CH2:17][C:26](=[O:28])[CH2:25][CH2:24][CH2:23]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1To a stirred boiling slurry made from potassium (1.28 g, 32.8 mmol) and t-BuOH (2.43 g, 32.8 mmol) in xylene (182.5 mL) under N2 was added diethyl 4,4′-(benzylazanediyl)dibutanoate (5 g, 14.9 mmol) over 5 hours in xylene (37.25 mL). The mixture was stirred and heated at reflux for 1 hour. After being cooled, the reaction mixture was neuturalized with 6N HCl (100 mL) and then was extracted with 6N HCl (3×50 mL). The combined acid solutions were filtered and the filtrate was heated under reflux for 1 hour. After cooling, the mixture was basified with concentrated KOH solution to pH 10 with cooling and extracted with dichloromethane. The combined organics were dried over Na2SO4 and concentrated to give a residue. Another 17 batches were done in parallel. The combined residue from 18 batches was purified together by column (P.E./EtOAc 5:1) to give 1-benzylazocan-5-one. 1H NMR (CDCl3, 400 MHz) δ 7.30-7.33 (m, 2H), 7.21-7.25 (m, 3H), 3.56 (s, 2H), 2.55 (t, J=6.0, 4H), 2.24 (t, J=6.4 Hz, 4H), 1.86-1.91 (m, 4H).
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