Butanal → Methyl 3-(4-(butylamino)phenyl)propanoate

Participants

Reaction Steps

Following a procedure analogous to that for the synthesis Example 106, methyl 3-(4-aminophenyl)propanoate (Jakobsen, C. M. et al., J. Med. Chem., 44:4696-4703 (2001)) (896 mg, 5.00 mmol) and butyraldehyde (397 mg, 5.50 mmol) were converted to the title compound (420 mg, 44%). 1H NMR (CDCl3) δ 7.01 (d, J=8.4 Hz, 2H), 6.60-6.47 (m, 2H), 3.68 (s, 3H), 3.10 (t, J=7.2 Hz, 2H), 2.89-2.77 (m, 2H), 2.62-2.46 (m, 2H), 1.66-1.53 (m, 2H), 1.43 (qd, J=15.0, 7.3 Hz, 2H), 0.96 (t, J=7.3 Hz, 3H); MS (ESI+) m/z 236.0 (M+H)+.

Provenance & Evidence