Gabapentin → HCID 22272023, compound

HRID 457296Notes

Reaction equation

HRID 457296 reaction equation
O=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH3:10])=[O:8].[CH2:11]1[CH2:16][CH2:15][C:14]([CH2:21][NH2:22])([CH2:17][C:18]([OH:20])=[O:19])[CH2:13][CH2:12]1.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>CO>[C:7]([C:3]1[CH2:4][CH2:5][CH2:6][C:2]=1[NH:22][CH2:21][C:14]1([CH2:17][C:18]([O-:20])=[O:19])[CH2:15][CH2:16][CH2:11][CH2:12][CH2:13]1)([O:9][CH3:10])=[O:8].[NH2+:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 3446GabapentinHCID 8082PiperidineHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

Product 1

HCID 22272023HCID 22272023, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-oxocyclopentanecarboxylate (124 μL, 1 mmol), gabapentin (171 mg, 1 mmol), and piperidine (99 μL, 1 mmol) were mixed in anhydrous methanol (10 mL). After heating under reflux for 16 h, the solvent was removed under reduced pressure to afford the title compound with purity greater than 90%. 1H NMR (CDCl3, 400 MHz): δ 1.29–1.60 (m, 12H), 1.72 (m, 4H), 1.79 (m, J=7.6 Hz, 2H), 2.24 (s, 2H), 2.49 (t, J=7.6 Hz, 2H), 2.55 (t, J=7.6 Hz, 2H), 2.99 (m, 4H), 3.24 (d, J=6.8 Hz, 2H), 3.63 (s, 3H), 5.06 (s, br, 2H), 7.93 (s, br, 1H). MS (ESI) m/z 294.36 (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-fc3557ee04044e6a89b0dfac602a9d54
Source dataset
uspto-grants-2007_03
Patent number
US07186855B2

Reaction notes

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