Oxalic Acid → HCID 14810850, compound

Participants

Reaction Steps

2[3-(1-Methylindol-3-yl)-1,2,4-oxadiazol-5-yl] ethene (0.4 g) was partially dissolved in ethanol. piperidine (2 ml) was added to the mixture and this was stirred for 10 minutes. Ethanol was evaporated under reduced pressure and excess piperidine was removed by heating under high vacuum. The residual oil crystallised upon refrigeration. The crude oil was converted to the monooxalate salt by treatment with 1 equivalent of oxalic acid in dichloromethane which afforded a white amorphous powder. This was recrystallised from ethanol yielding the title compound m.p. 186°-188° C. Found: C, 59.85; H, 6.10; N, 13.95; C18H22N4O.(COOH)2 requires C, 59.99; H, 6.04; N, 13.99%; δH (360 MHz, D2O) 1.48-2.06 (8 H, m, CH2 pip: NCH2CH2 ×2+NCH2CH2CH2), 3.00-3.08 (2 H, m, NCH2) 3.50 (2 H, t, J=9 Hz, CH2CH2N, 3.58-3.70 (4 H, m, CH2CH2N+NCH2CH2 pip, overlapping), 3.87 (3 H, s, NCH3), 7.36 (dt, 1 H, J=7.2, 1.1 Hz, H-5 or H-6), 7.42 (1 H, d, J=7.2, 1.1 Hz, H-5 or H-6) 7.58 (1 H, d, J=8.2 Hz, H-7), 7.89 (s, 1 H, H-2), 8.00 (1 H, d, J=7.5 Hz, H-4); m/z (CI+) 311 (M+ +1, 100%), 226 (30), 157 (70), 98 (90).

Provenance & Evidence