Gabapentin → HCID 66584324, compound

HRID 384555Notes

Reaction equation

HRID 384555 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=O)[CH3:5].[CH2:8]1[CH2:13][CH2:12][C:11]([CH2:18][NH2:19])([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH2:9]1.[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>CO>[CH3:5][C:4]([NH:19][CH2:18][C:11]1([CH2:14][C:15]([O-:17])=[O:16])[CH2:12][CH2:13][CH2:8][CH2:9][CH2:10]1)=[CH:3][C:2](=[O:7])[CH3:1].[NH2+:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 3446GabapentinHCID 8082PiperidineHCID 31261Acetylacetone

Product 1

HCID 66584324HCID 66584324, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,4-pentanedione (103 μL, 1 mmol), gabapentin (171 mg, 1 mmol), and piperidine (99 μL, 1 mmol) were mixed in anhydrous methanol (10 mL). The resulting mixture was heated under reflux for 4 h. Removal of the solvent under reduced pressure gave the title compound with purity greater than 90%. 1H NMR (CDCl3, 400 MHz): δ 1.34-1.62 (m, 12H), 1.71 (m, 4H), 1.94 (s, 3H), 1.96 (s, 3H), 2.26 (s, 2H), 2.98 (m, 4H), 3.38 (d, J=6 Hz, 2H), 4.90 (s, 1H), 5.20 (s, br, 2H), 8.64 (t, J=6 Hz, 1H). MS (ESI) m/z 252.35 (M−H−).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 4 h
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b62ee56342c644f1872f74de63b2631d
Source dataset
uspto-grants-2013_02
Patent number
US08367722B2

Reaction notes

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