Gabapentin → HCID 66584283, compound

HRID 384556Notes

Reaction equation

HRID 384556 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][O:7][C:5]1=[O:6])(=O)[CH3:2].[CH2:10]1[CH2:15][CH2:14][C:13]([CH2:20][NH2:21])([CH2:16][C:17]([OH:19])=[O:18])[CH2:12][CH2:11]1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CO>[O:6]=[C:5]1[C:4](=[CH:1][CH2:2][NH:21][CH2:20][C:13]2([CH2:16][C:17]([O-:19])=[O:18])[CH2:14][CH2:15][CH2:10][CH2:11][CH2:12]2)[CH2:9][CH2:8][O:7]1.[NH2+:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 3446GabapentinHCID 8082PiperidineHCID 106012-Acetylbutyrolactone

Product 1

HCID 66584283HCID 66584283, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Acetylbutyrolactone (108 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 6 h, the solvent was removed under reduced pressure to afford the title compound with purity greater than 90%. 1H NMR (CDCl3, 400 MHz): δ 1.34-1.62 (m, 12H), 1.71 (m, 4H), 1.94 (s, 3H), 2.24 (s, 2H), 2.81 (t, J=7.6 Hz, 2H), 2.99 (m, 4H), 3.31 (d, J=6.4 Hz, 2H), 4.23 (t, J=7.6 Hz, 2H), 5.17 (s, br, 2H), 8.64 (t, J=6.4 Hz, 1H). MS (ESI) m/z 280.34 (M−H−).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 6 h
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4c23cddfa8874396b09c431ae6fab303
Source dataset
uspto-grants-2013_02
Patent number
US08367722B2

Reaction notes

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