(1,4'-Bipiperidine)-4'-carboxamide → HCID 22185336, compound

Participants

Reaction Steps

In a three neck round-bottom flask equipped with a stirring bar, reflux condenser, and rubber septa is placed [1,4′]bipiperidinyl-4′-carboxylic acid amide (5.01 g, 23.7 mmol) in 140 mL of anhydrous 1-propanol and the solution is heated to reflux. Sodium metal (˜9.276 g, 403.4 mmol) rinsed in hexane to remove mineral oil) is added in portions. Once the sodium metal completely dissolves, the mixture is allowed to stir over the weekend. The reaction mixture is cooled to room temperature and the solvent removed under reduced pressure. Distilled water is added and the solution extracted with chloroform. The organic layer is collected, dried over sodium sulfate, filtered, and the solvent removed under reduced pressure to afford 4.4 g of the desired product which is used without further purification. 1H NMR (CD3OD, 300 MHz) δ 1.48–1.60 (m, 8H), 1.72–1.80 (m, 2H), 2.61–2.71 (m, 6H), 2.92–3.01 (m, 2H), 3.37 (s, 1H), 3.56 (s, 2H). MS (ESI) m/z 199 (M+H+).

Provenance & Evidence