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

HRID 488579Notes

Reaction equation

HRID 488579 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-1a8aa56f66064928a9b65ba53021205d
Source dataset
uspto-grants-2005_12
Patent number
US06972341B2

Reaction notes

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