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

HRID 591174Notes

Reaction equation

HRID 591174 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-8dccb5567d3d40c986162af24b5478d5
Source dataset
uspto-grants-2016_01
Patent number
US09238616B2

Reaction notes

Loading…