Reaction #544477

Reaction equation

2-Acetylbutyrolactone

gabapentin

piperidine

→

title compound

Piperidinium 1-{1-[(2-Oxo-Tetrahydrofuran-3-ylidene)ethyl]aminomethyl}-1-Cyclohexane Acetate

Solvents

methanol

Conditions

Workup

1. 1
   TemperatureAfter heating
2. 2
   Temperatureunder reflux for 6 h
3. 3
   Otherthe solvent was removed under reduced pressure

Procedure

2-Acetylbutyrolactone (108 μL, 1 mmol), gabapentin (171 mg, 1 mmol), and piperidine (99 μL, 1 mmol) were mixed in anhydrous methanol (10 mL). After heating under reflux for 6 h, the solvent was removed under reduced pressure to afford the title compound with purity greater than 90%. 1H NMR (CDCl3, 400 MHz): δ 1.34–1.62 (m, 12H), 1.71 (m, 4H), 1.94 (s, 3H), 2.24 (s, 2H), 2.81 (t, J=7.6 Hz, 2H), 2.99 (m, 4H), 3.31 (d, J=6.4 Hz, 2H), 4.23 (t, J=7.6 Hz, 2H), 5.17 (s, br, 2H), 8.64 (t, J=6.4 Hz, 1H). MS (ESI) m/z 280.34 (M−H−).

Source