1-Phenylpiperazine → HCID 57682692, compound

Participants

Reaction Steps

To a solution of di-tert-butyl tricarbonate (60 mg, 0.23 mmol) in DCM (1 ml) was added in one portion, a solution of 7-aminoquinoline (D55) (30 mg, 0.21 mmol) in DCM (1 ml). After 5 mins, when gas evolution was complete, tris -amine resin (12 mg 0.04 mmol) was added, then after 1 h a solution of 4-phenylpiperazine (32 ul, 0.21 mmol) was added and the reaction stirred at room temperature overnight. The reaction mixture was then purified directly by SPE column chromatography, eluting with an EtOAc/60-80° C.-petroleum ether gradient, followed by treatment with excess methyl isocyanate resin to remove unreacted 7-aminoquinoline starting material from the product. On completion the resin was removed by filtration and filtrate concentrated in vacuo to give the title compound as an orange gum. 1H NMR (250 MHz, CDCl3) δ (ppm): 8.85 (dd, 1H), 8.09 (dd, 1H), 7.93 (dd, 1H), 7.82 (s, 1H), 7.76 (d, 1H), 7.30 (m, 3H), 6.94 (m, 3H), 6.83 (br, 1H), 3.72 (m, 4H), 3.28 (m, 4H).

Provenance & Evidence