Diisopropylethylamine → HCID 68106834, compound

Temperature

130 °C

3-Chloro-4-fluorobenzoic acid (1 g) was dissolved in N,N-dimethylacetamide (10 ml), and tert-butyl piperazine-1-carboxylate (1.3 g) and DIPEA (1.9 g) were added thereto, followed by stirring at 130° C. overnight. The reaction mixture was concentrated under reduced pressure, and a 1 M aqueous NaOH solution was added thereto, followed by washing with EtOAc. The pH of the aqueous layer was adjusted to around 6 to 7 by the addition of 1 M hydrochloric acid, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH). The product was dissolved in dioxane (10 ml), and 4 M hydrogen chloride/dioxane (10 ml) was added thereto, followed by stirring at room temperature overnight. The precipitated solid was collected by filtration to obtain 3-chloro-4-piperazin-1-yl benzoic acid hydrochloride (142 mg).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additiona 1 M aqueous NaOH solution was added
3. washby washing with EtOAc
4. additionThe pH of the aqueous layer was adjusted to around 6 to 7 by the addition of 1 M hydrochloric acid
5. extractionfollowed by extraction with CHCl3
6. dry with materialThe organic layer was dried over Na2SO4
7. concentrationthe solvent was concentrated under reduced pressure
8. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)
9. dissolutionThe product was dissolved in dioxane (10 ml)
10. addition4 M hydrogen chloride/dioxane (10 ml) was added
11. stirringby stirring at room temperature overnight
12. filtrationThe precipitated solid was collected by filtration

ORD record

ord-1d32516c51554573b3d580b71d42637f

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802679B2