Sodium Iodide → HCID 10781757, compound

Participants

Reaction Steps

A mixture of (+)-11-chloro-2,3,11,11a-tetrahydro-1H,5H,-pyrrolo[2,1-c][1,4]benzothiazepin-5-one (38)15 (0.6 g, 2.4 mmol), freshly distilled 1-methylpiperazine (0.34 mL, 3.1 mmol), Na2CO3(1.06 g, 10.0 mmol), NaI (0.36 g, 2.4 mmol) in dry CH3CN (30 mL) was gently refluxed for 20 hours. The solvent was evaporated and the residue was partitioned between CH2Cl2 and water. The organic phase was successively washed with a 2% solution of Na2S2O3, water and brine. The residue obtained after evaporation was chromatographed on silica gel eluting with 5% methanol in CH2Cl2. The title compound 27 was obtained as a white solid (0.55 g, 73% yield): mp 188–190° C. (2-propanol-isopropyl ether); IR (KBr) 1630 cm−1; 1H NMR (CDCl3) δ7.71 (m, 1H), 7.50 (m, 2H), 7.61 (m, 1H), 7.33 (m, 2H), 4.36 (d, 1H, J=11.2 Hz), 3.70 (m, 3H), 2.58 (m, 4H), 2.38 (m, 4H), 2.27 (s, 3H), 2.02 (m, 4H). MS m/z 317 (100, M+), 217, 180, 139, 99, 70. Anal. (C17H23N3OS)C, H, N.

Provenance & Evidence