[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH2:13][NH2:14])[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.[C:17]1([CH2:23][CH2:24][CH2:25][CH:26]=O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[CH2:13][NH:14][CH2:26][CH2:25][CH2:24][CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1To a mixture of (3-(4-fluorophenoxy)phenyl)methanamine (200 mg, 0.092 mmol, 1.0 eq) in methanol was added 4-phenylbutanal (136 mg, 0.92 mmol, 1.0 eq). The mixture was refluxed for 2 h, then cooled to 0° C., before adding NaBH4 (105 mg, 2.76 mmol, 3.0 eq) portion wise. The mixture was stirred for 15 minutes before being quenched with 10% aq. NaHCO3 solution. The volatiles were evaporated under reduced pressure and the aqueous solution obtained was extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the desired compound (200 mg, 62%); 1H NMR (400 MHz, CD3OD) δ 7.33-6.86 (m, 13H), 3.72-3.50 (s, 2H), 2.63-2.50 (m, 4H), 1.65-1.54 (m, 4H). MS (ESI): 350.2 (M+H)+.
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