n-[3-(3,4-Dichloro-phenyl)-propyl]-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-n-methoxy-acetamide → 4-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid [3-(3,4-dichlorophenyl)-propyl]-methoxy-amide

Participants

Reaction Steps

Reaction of N-[3-(3,4-dichlorophenyl)-propyl]-2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-methoxy-acetamide (0.378 g, 0.97 mmol) with the paraformaldehyde-N-(2-aminoethyl)morpholine adduct in methanol using a procedure similar to the one described in the preparation of compound 13 gave 0.196 g (42% yield) of the title compound as a solid after chromatography on reversed phase silica gel. 1HNMR 400 MHz (CDCl3) δ (ppm); 1.98 (2H, m, CH2), 2.49 (4H, broad, 2×NCH2), 2.58 (2H, t, J=6.2 Hz, CH2), 2.63 (2H, t, J=7.5 Hz, CH2), 3.63 (2H, t, J=6.2 Hz, NCH2), 3.68 (4H, broad, 2×OCH2), 3.71 (3H, s, OCH3), 3.74 (2H, t, J=7.0 Hz, NCH2), 4.23 (2H, s, NCH2), 7.02 (1H, dd, J=2.0 Hz and J=8.2 Hz, aromatic), 7.28 (1H, d, J=2.0 Hz, aromatic), 7.34 (1H, d, J=8.2 Hz, aromatic). HRMS (FAB+) calculated for C21H28Cl2N3O5: [M+H]+: 472.140602. found: 472.138651.

Provenance & Evidence