Diisopropylethylamine → HCID 43215774, compound

To a solution of ethyl 4-fluoro-3-nitrobenzoate (2.13 g) and 1-methylpiperidin-4-amine (1.14 g) in tetrahydrofuran (40 mL) was added N,N-diisopropylethylamine (5 mL). The mixture was then stirred at reflux overnight. The solvent was evaporated and the residue was dissolved in ethyl acetate (300 mL) and washed with aqueous NaHCO3, water and brine. After evaporation of the solvent, the residue was dissolved in tetrahydrofuran (20 mL), methanol (10 mL) and water (10 mL). Then, LiOH H2O (2 g) was added. The mixture was stirred at room temperature overnight. The mixture was then concentrated and the residue was neutralized with 5% aqueous HC. The precipitate was filtered, washed with brine, and dried under vacuum to give the product.

1. temperatureat reflux overnight
2. customThe solvent was evaporated
3. dissolutionthe residue was dissolved in ethyl acetate (300 mL)
4. washwashed with aqueous NaHCO3, water and brine
5. customAfter evaporation of the solvent
6. dissolutionthe residue was dissolved in tetrahydrofuran (20 mL)
7. additionThen, LiOH H2O (2 g) was added
8. stirringThe mixture was stirred at room temperature overnight
9. concentrationThe mixture was then concentrated
10. filtrationThe precipitate was filtered
11. washwashed with brine
12. customdried under vacuum
13. customto give the product

ORD record

ord-789ef7491a164d878fd6f66a3ab4143d

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09303025B2