1-Phenylpiperazine → HCID 57682692, compound

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).

1. customThe reaction mixture was then purified directly by SPE column chromatography
2. washeluting with an EtOAc/60-80° C.-petroleum ether gradient
3. customto remove unreacted 7-aminoquinoline starting material from the product
4. customOn completion the resin was removed by filtration and filtrate
5. concentrationconcentrated in vacuo

ORD record

ord-3e53c10e6c4b40d3ba3a9925b371c1af

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538121B2