1,4'-Bipiperidine → HCID 86753925, compound

Participants

Reaction Steps

To a suspension of (±)-7-[1-[(iodoacetyl)oxy]propyl]-8-methylindolizino[1,2-b]quinolin-9(11H)-one (50 mg, 0.11 mmol) in CH2Cl2 (4 mL) was added 4-piperidinopiperidine (17.6 mg, 0.11 mmol). After stirring at room temperature for 3.5 h, thin layer chromatographic analysis indicated that the reaction was incomplete,. Additional 4-piperidinopiperidine (2.7 mg, 0.016 mmol) was added, and stirring was continued for 2 d. The mixture was concentrated under reduced pressure, and the residue was purified by column chromatography eluting with a solvent gradient of 0-100% MeOH in H2O containing 1% HOAc. The title compound was obtained after lyophilization. 1H NMR (CDCl3) d 8.35 (s, 1H), 8.21 (d, J=8.4 Hz, 1H), 7.92 (d, J=8.3 Hz, 1H), 7.83 (m, 1H), 7.63 (m, 1H), 7.34 (s, 1H), 5.94 (apparent t, 1H), 5.26 (s, 2H), 3.32 (s, 2H), 3.00 (br m, 2H), 2.37 (s, 3H), 2.6-1.4 (m, 13H), 0.98 (t, J=7.4 Hz, 3H). Anal. Calcd for C31H38N4O3.1/4 HI.3/8 H2O: C, 67.28; H, 7.10; N, 10.12. Found: C, 67.67; H, 6.79; N, 9.69.

Provenance & Evidence