Triethylamine → HCID 59694185, compound

To a suspension of 3,5-dichloroisonicotinic acid (250 mg, 1.30 mmol) in CH2Cl2 (6.5 mL) was added DMF (cat.) and oxalyl chloride (0.45 mL, 5.2 mmol), and the mixture was stirred at room temperature for 2 h then concentrated in vacuo. To the residue was added THF (2 mL), Et3N (0.27 mL, 1.9 mmol), and a solution of 3-piperidinemethanol (150 mg, 1.30 mmol) in THF (4.5 mL), and the mixture was stirred at room temperature for 21 h. The mixture was diluted with CH2Cl2 (50 mL) and brine (30 mL) and the phases were separated. The organic layer was washed with brine (2×50 mL) and saturated NaHCO3 (2×50 mL). The organic layer was dried (MgSO4), filtered, concentrated, and dried in vacuo to afford a crude oil. Purification of the crude material by column chromatography on silica gel (100:5:1 CH2Cl2/MeOH/NH4OH) gave a yellow oil (mixture of isomers) (147 mg, 39%). 1H NMR (CDCl3) δ 1.28-1.96 (m, 4H), 2.89-3.26 (m, 3H), 3.35-3.45 (m, 1H), 3.50-3.72 (m, 2H), 4.29-4.56 (m, 1H), 8.54 (m, 2H).

1. concentrationthen concentrated in vacuo
2. customthe phases were separated
3. washThe organic layer was washed with brine (2×50 mL) and saturated NaHCO3 (2×50 mL)
4. dry with materialThe organic layer was dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customdried in vacuo
8. customto afford a crude oil
9. customPurification of the crude material by column chromatography on silica gel (100:5:1 CH2Cl2/MeOH/NH4OH)
10. customgave
11. additiona yellow oil (mixture of isomers) (147 mg, 39%)

ORD record

ord-b92b7502616e48c4bdf8a4746d1651b9

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778967B2