Cl.[CH2:2]([NH:4][CH2:5][CH3:6])[CH3:3].[C-:7]#[N:8].[K+].CO.C1COCC1.[CH2:17]([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC>[CH2:17]([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]([N:4]([CH2:5][CH3:6])[CH2:2][CH3:3])[C:7]#[N:8])=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Diethylamine hydrochloride (76.7 g, 70 mmol) was added portion wise at rt to a 200 mL aqueous solution of potassium cyanide (45.5 g, 70 mmol) with stirring and warmed to 60°-65° C. A MeOH/THF (300 ml, 1:1) solution of 4-(benzyloxy)-benzaldehyde (100 g, 47 mmol) (Aldrich) was added in a thin stream to the aqueous solution and stirred for 16 hr at ~62° C. The reaction mixture was allowed to cool and the organics were removed in vacuo. The aqueous portion was diluted with an equal volume of brine and extracted several times with EtOAc. The EtOAc extracts were combined, washed with H2O, dried (Na2SO4), and concentrated to a tacky amber solid. The material was triturated with petroleum ether and filtered to give a yellow solid, which was taken up in warm Et2O, charcoaled, filtered, diluted with petroleum ether, and allowed to crystallize. The crystals were filtered and dried in vacuo to give 81.5 g (59%) of the desired product: mp 75°-76° C.; 1H NMR (CDCl3) d 1.06-1.11 (t, 6H, J=7 Hz, CH3), 2.42-2.49 (m, 2H, NCH2), 2.66-2.73 (m, 2H, NCH2), 4.98 (s, 1H, CHCN), 5.09 (s, 2H, OCH2), 6.99-7.01 (d, 2H, J=7 Hz, ArH), 7.35-7.49 (m, 7H, ArH); MS(FD) 294(M+). Anal. Calcd for C19H22N2O: C, 77.52; H, 7.53; N, 9.51. Found: C, 77.70; H, 7.64; N, 9.45.
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