Gabapentin → HCID 22272023, compound

HRID 591173Notes

Reaction equation

HRID 591173 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-a0df10dfcc73487e98f306cc11615569
Source dataset
uspto-grants-2016_01
Patent number
US09238616B2

Reaction notes

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