Dibenzylamine → HCID 66587380, compound

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Reaction Steps

The product was prepared by above general procedure and the same chemicals except employing dibenzylamine (1a′) (98 mg, 0.5 mmol), and pent-4-enal (2d′) (63 mg, 0.75 mmol). After 24 h, the crude product was purified by flash column chromatography (silica gel; ethyl acetate or diethyl ether/hexane=1:100) to afford the desired product 3d as a light yellowish oil (0.102 g, 63% yield); Rf=0.70 (hexane:ethyl acetate=3:1); 1H NMR (CDCl3, 400 MHz) δ 7.38-7.37 (m, 4H), 7.30-7.26 (m, 4H), 7.21-7.18 (m, 2H), 5.89-5.79 (m, 1H), 5.08-5.00 (m, 2H), 4.39-4.38 (d, J=4.93 Hz, 1H), 3.80-3.71 (m, 4H), 3.35 (s, 3H), 3.28 (s, 3H), 2.89-2.84 (m, 1H), 2.44-2.26 (m, 2H) ppm; C NMR (CDCl3, 100 MHz) δ 140.5 (C×2), 137.8, 129.0 (CH×4), 128.0 (CH×4), 126.7 (CH2×2), 115.5, 107.0, 57.8, 54.7, 54.5, 54.4 (CH2×2), 31.2 ppm; FTIR (neat): v=3015, 1454, 1215, 754, 700, 494 cm−1; HRMS (ESI, m/z): calcd for C21H28NO2+ [M+H]+ 326.2120, found: 326.2114.

Provenance & Evidence