Trifluoroacetic acid → HCID 21101690, compound

Participants

Reaction Steps

4-Chloro-6,7-methylenedioxyquinoline [obtained from 3,4-methylendioxyaniline following the protocol of Krogstad et. al. (De, D., Byers L. D., Krogstad, D. J. J. Heterocyclic Chem. 1997, 34, 315; 1H NMR ([D]6-DMSO), δ 6.28 (s, 2H), 7.45 (s, 1H), 7.50 (s, 1H), 7.65 (d, 1H), 8.62 (d, 1H)) (0.50 g, 2.4 mmol) and 1-tert-butoxycarbonylpiperazine (1.8 g, 9.6 mmol) are reacted according to method A yielding 391 mg of 4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-6,7-methylenedioxy quinoline. After cleaving the Boc group with trifluoroacetic acid (1.5 mL) in CH2Cl2 (1.5 mL), the piperazine is treated with 4-fluorophenylisocyanate (86 μL) and triethylamine (0.245 mL) according to method C yielding the title product.

Provenance & Evidence