Gabapentin → HCID 22272023, compound

HRID 1710436Notes

Reaction equation

HRID 1710436 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-aad4518e7297447785dea99fc199a58d
Source dataset
uspto-grants-2010_09
Patent number
US07790708B2

Reaction notes

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