Triethylamine → HCID 59694185, compound

Participants

Reaction Steps

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).

Provenance & Evidence