Piperazine → HCID 10133817, compound

Participants

Reaction Steps

To a solution of piperazine (16.144 g, 186.4 mmol) in CH2Cl2 (80 mL) stirred in an ice-brine bath was added dropwise of a solution of compound 23 (3.009 g, 9.35 mmol) in CH2Cl2 (270 mL) over the course of two days. The reaction was then stirred for 74 hrs, whereupon the starting material was consumed (TLC, 5% MeOH in CH2Cl2). The reaction mixture was partitioned between CH2Cl2 and water. The organic layer was then washed with saturated sodium chloride solution and dried over anhydrous MgSO4. The organic layer was then concentrated in vacuo, redissolved in a minimal amount of CH2Cl2, and chromatographed over normal phase silica (MeOH/CH2Cl2). The fractions containing the desired product were combined and concentrated in vacuo to yield an light yellow oil. The oil was then triturated with CH2Cl2/diisopropyl ether and vacuum filtered to afford compound 24 as a white powder (2.032 g, 58.5% yield, 95.5% HPLC purity). 1H NMR (500 MHz, DMSO-d6): δ 8.21 (d, J=2 Hz, 1H), 8.03 (dd, J1=9 Hz, J2=2 Hz, 1H), 7.01 (m, 1H), 6.96 (d, J=11 Hz, 1H), 6.80 (d, J=9 Hz, 2H), 3.19 (m, 2H), 3.11 (m, 2H), 2.70 (m, 2H), 2.46 (m, 2H), 2.30 (s, 1H), 2.27 (s, 6H).

Provenance & Evidence