Reaction #471737

Reaction equation

2,4-pentanedione

gabapentin

piperidine

→

title compound

Piperidinium 1-{(1-Methyl-3-Oxo-But-1-enyl)aminomethyl}-1-Cyclohexane Acetate

Solvents

methanol

Conditions

Workup

1. 1
   TemperatureThe resulting mixture was heated
2. 2
   Temperatureunder reflux for 4 h
3. 3
   OtherRemoval of the solvent under reduced pressure

Procedure

2,4-pentanedione (103 μL, 1 mmol), gabapentin (171 mg, 1 mmol), and piperidine (99 μL, 1 mmol) were mixed in anhydrous methanol (10 mL). The resulting mixture was heated under reflux for 4 h. Removal of the solvent under reduced pressure gave 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), 1.96 (s, 3H), 2.26 (s, 2H), 2.98 (m, 4H), 3.38 (d, J=6 Hz, 2H), 4.90 (s, 1H), 5.20 (s, br, 2H), 8.64 (t, J=6 Hz, 1H). MS (ESI) m/z 252.35 (M−H−).

Source