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

HRID 1919342Notes

Reaction equation

HRID 1919342 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-7bc47aa755494cb9bd4b3804c1a63860
Source dataset
uspto-grants-2012_05
Patent number
US08168623B2

Reaction notes

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