HCID 67655068, compound → HCID 54555986, compound

Participants

Reaction Steps

Reaction of Intermediate 2 with 4-nitrobenzaldehyde under standard reductive amination conditions gave 1-(3-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl)-4-(4-(nitro)benzyl)piperazine in 46% yield. PtO2 (60 mg) was suspended in ethanol (40 ml) and stirred under an atmosphere of hydrogen for 0.75 h. The preceding nitrobenzyl piperazine (0.33 g, 0.74 mmol) was then added and the mixture stirred for 2 h. The catalyst was removed by filtration through celite, the solvent removed under vacuum and the residue chromatographed on silica gel eluting with CH2Cl2 /MeOH/NH3 (70:8:1) to give the title-amino-benzyl piperazine (0.26 g, 85%). The 4.1 hydrogen oxalate salt was prepared: mp 150°-153° C. (Found: C, 49.04; H, 4.80; N, 12.76. C24H29N7.4.1(C2H2O4) requires C, 49.28; H, 4.77; N, 12.49%); m/e 416 (M+1)+ ; δ (250 MHz, d6 -DMSO; free base) 1.72-1.86 (2H, m, CH2); 2.16-2.44 (10H, m, 5 of CH2); 2.70 (2H, t, J=7.4Hz, CH2); 3.23 (2H, s, CH2); 4.93 (2H, s, NH2); 6.48 (2H, d, J=8.4Hz, Ar-H); 6.89 (2H, d, J=8.4Hz, Ar-H); 7.27 (1H, s, Ar-H); 7.29 (1H, dd, J=2.1 and 8.6Hz, Ar-H); 7.47 (1H, d, J=8.6Hz, Ar-H); 7.78 (1H, d, J=2.1Hz, Ar-H); 9.02 (2H, s, Triazole-H); 11.07 (1H, s, NH).

Provenance & Evidence