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Hydrogenation of aniline 12 and 2-phenylacetaldehyde gives 3-hydroxy-3-(3-(phenethylamino)phenyl)propanenitrile. A mixture of aniline 12 (1.00 g, 6.17 mmol), 2-phenylacetaldehyde (0.66 g, 5.55 mmol) and A-3 molecular sieves in MeOH was stirred for 18 h and then NaBH4 (1.16 g, 30.8 mmol) was added and the reaction mixture was stirred overnight. The reaction mixture was filtered through Celite, concentrated under reduced pressure. Purification by column chromatography (100-200 silica mesh, 20% EtOAc—hexane) gave 3-hydroxy-3-(3-(phenethylamino)phenyl)propanenitrile as a yellow liquid. Yield (0.432 g, 27%); 1H NMR (400 MHz, DMSO-d6) δ 7.32-7.26 (m, 4H), 7.20 (t, J=6.4 Hz, 1H), 7.04 (t, J=7.6 Hz, 1H), 6.64 (s, 1H), 6.55 (d, J=7.2 Hz, 1H), 6.50 (d, J=8.4 Hz, 1H), 5.77 (d, J=4.4 Hz, 1H), 5.68 (t, J=5.6 Hz, 1H), 4.76-4.72 (m, 1H), 3.26-3.21 (m, 2H), 2.85-2.81 (m, 3H), 2.79-2.72 (m, 1H).

1. stirringthe reaction mixture was stirred overnight
2. filtrationThe reaction mixture was filtered through Celite
3. concentrationconcentrated under reduced pressure
4. customPurification by column chromatography (100-200 silica mesh, 20% EtOAc—hexane)