Diisopropylethylamine → HCID 178516934, compound

Temperature

0 °C

In a three-neck flask equipped with argon inlet was charged with rhodanine (200 mg, 1.5 mmol, 1.4 eq), anhydrous Acetonitrile (5 mL), 2-(4-fluoro-phenyl)-cyclopropylamine HCl salt (200 mg, 1.1 mmol, 1 eq) and diisopropylehtylamine (0.58 mL, 3 eq). The mixture was cooled to 0° C. and mercury (II) chloride (376 mg, 1.3 eq) was added. The reaction mixture was stirred at 0° C. for 30 minutes and room temperature for another 1.5 hours. The reaction mixture was filtered through a celite cake and washed with dichloromethane (3×20 mL), methanol (3×20 mL) and diethyl ether (3×20 mL). The filtrate and washing solutions were combined and concentrated by rotavaping to afford crude product. The crude was purified by flash chromatography (40 gram prepacked column by Isco, Inc., 230400 mesh, eluant: 0-10% methanol in dichloromethane) to obtain 136 mg of pure product. The structure was confirmed with

1. customIn a three-neck flask equipped with argon inlet
2. filtrationThe reaction mixture was filtered through a celite cake
3. washwashed with dichloromethane (3×20 mL), methanol (3×20 mL) and diethyl ether (3×20 mL)
4. washThe filtrate and washing solutions
5. concentrationconcentrated
6. customto afford crude product
7. customThe crude was purified by flash chromatography (40 gram prepacked column by Isco, Inc., 230400 mesh, eluant: 0-10% methanol in dichloromethane)

ORD record

ord-2992df65a7714a03addc7350b7f2c81a

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07253285B2