Gabapentin → Piperidinium 1-{(1-Methyl-2-(Ethoxycarbonyl)-3-Ethoxy-3-Oxoprop-1-enyl)aminomethyl}-1-C yclohexane Acetate

HRID 1710437Notes

Reaction equation

HRID 1710437 reaction equation
[C:1]([CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)[CH3:2].[CH2:15]1[CH2:20][CH2:19][C:18]([CH2:25][NH2:26])([CH2:21][C:22]([OH:24])=[O:23])[CH2:17][CH2:16]1.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(O)C>[CH3:2][C:1]([NH:26][CH2:25][C:18]1([CH2:21][C:22]([O-:24])=[O:23])[CH2:19][CH2:20][CH2:15][CH2:16][CH2:17]1)=[C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2+:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 3446GabapentinHCID 8082PiperidineHCID 1363651,3-Diethyl 2-acetylpropanedioate

Product 1

HCID 22272000Piperidinium 1-{(1-Methyl-2-(Ethoxycarbonyl)-3-Ethoxy-3-Oxoprop-1-enyl)aminomethyl}-1-C yclohexane Acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl acetylmalonate (202 mg, 1 mmol), gabapentin (171 mg, 1 mmol), and piperidine (99 μL, 1 mmol) were mixed in anhydrous ethanol (10 mL). After heating under reflux for 16 h, the solvent was removed under reduced pressure to give the title compound with purity greater than 90%. 1H NMR (CDCl3, 400 MHz): δ 1.28 (t, J=7.2 Hz, 6H), 1.38-1.64 (m, 12H), 1.75 (m, 4H), 1.96 (s, 3H), 2.23 (s, 2H), 2.99 (m, 4H), 3.24 (d, J=5.2 Hz, 2H), 4.20 (q, J=7.2 Hz, 4H), 4.35 (s, br, 2H), 7.79 (t, J=5.2 Hz, 1H). MS (ESI) m/z 354.38 (M−H−).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 16 h
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3e64ba35a8b449058b7540441e7831a0
Source dataset
uspto-grants-2010_09
Patent number
US07790708B2

Reaction notes

Loading…