Gabapentin → HCID 22272023, compound

HRID 488578Notes

Reaction equation

HRID 488578 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-360861abaf96415e99d52b60d2c0a4b3
Source dataset
uspto-grants-2005_12
Patent number
US06972341B2

Reaction notes

Loading…