Hydrochloric Acid → 1-(2-(2,5-Dichlorophenoxy)-5-nitrophenylsulfonyl)piperazine

To a solution of compound 39 (0.100 g, 0.19 mmol) in DCM (6.00 mL) was added 1N HCl in 1,4-dioxane (0.570 mL). The reaction was monitored with TLC (25% EtOAc in hexanes, Rf=0.0). The reaction was complete after stirring at room temperature for 16 hrs, as indicated by the absence of the starting material). The reaction mixture was concentrated and the residual was redissolved in MeOH (2.00 mL). Et2O (4.00 mL) was then added and the mixture was stirred until precipitate formed (10 min). The solid was collected by filtration to yield compound 147 as a white solid (0.080 g, 100% HPLC purity, 83% yield). 1H NMR (500 MHz, DMSO-d6): δ 9.39 (s, 2H), 8.61 (d, J=2 Hz, 1H), 8.45 (dd, J1=3 Hz, J2=9 Hz, 1H), 7.78 (d, J=9 Hz, 1H), 7.73 (d, J=2 Hz, 1H), 7.53 (dd, J1=2 Hz, J2=8 Hz, 1H), 7.12 (d, J=8 Hz, 1H), 3.57 (m, 4H), 3.16 (m, 4H).

1. concentrationThe reaction mixture was concentrated
2. dissolutionthe residual was redissolved in MeOH (2.00 mL)
3. additionEt2O (4.00 mL) was then added
4. stirringthe mixture was stirred until precipitate
5. customformed (10 min)
6. filtrationThe solid was collected by filtration

ORD-Eintrag

ord-bda50d99dea34530ad77fbbcd37f1642

Quelldatensatz

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08399456B2