1-Methylpiperazine → 2-(5-Acetyl-2-ethylamino-phenylimino)-3-benzyl-5-(4-methylpiperazin-1-ylmethylene)-thiazolidin-4-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-methylpiperazine (0.22 mL, 2.0 mmol) in N,N-dimethylformamide dimethyl acetal (1.5 mL) was heated at 100° C. After 3 h, the mixture was concentrated under reduced pressure and diluted with toluene (2 cycles), and then concentrated under vacuum. Next an aliquot (80 μL) of the concentrated intermediate was added to a solution of 2-(5-acetyl-2-ethylamino-phenylimino)-3-benzyl-thiazolidin-4-one (60 mg, 0.16 mmol) in toluene (1.0 mL, anhyd). After heating at 120° C. for 1 h, the mixture was cooled, concentrated and chromatographed (silica gel, DCM to 0.2:10:89.8 DEA/MeOH/DCM) to yield the title product (61 mg, 78%) as a yellow solid. 1H-NMR (CDCl3): δ 7.66 (1H, dd), 7.58 (1H, d), 7.55 (1H, s), 7.27-7.42 (5H, m), 6.49 (1H, d), 5.11 (2H, s), 4.12 (1H, br t), 3.45 (4H, br t), 3.03 (2H, m), 2.49 (3K, s), 2.43 (4H, br t), 2.30 (3H, s), 1.02 (3H, t); MS (ESI): 478 (MH+).

Provenance & Evidence