Potassium Hydroxide → Gabapentin

HRID 1972180Notes

Reaction equation

HRID 1972180 reaction equation
[CH2:1]1[CH2:6][CH2:5][C:4]([CH2:11][NH2:12])([CH2:7][C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1.Cl.[OH-].[K+]>C(O)C1C=CC=CC=1>[CH2:1]1[CH2:2][CH2:3][C:4]([CH2:11][NH2:12])([CH2:7][C:8]([OH:10])=[O:9])[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 6453919Gabapentin hydrochloride

Product 1

HCID 3446Gabapentin

Reagents, catalysts & solvents 1

HCID 244Benzyl AlcoholSolvent

Conditions

Temperature
2.5 °C

Procedure

Gabapentin hydrochloride (10 g, 0.048 mol) was dissolved in benzyl alcohol (70 ml) at room temperature. Finely powdered potassium hydroxide (2.7 g, 0.048 mol) was added and the reaction mixture was stirred till the solution pH reaches 7.0 to 7.5. It will take about 2 to 3 hours. The suspension was filtered and the residue washed with about 5 ml benzyl alcohol. The clear filtrate was cooled to 0-5° C. and 140 ml of methyl tert.butyl ether (MTBE) was added. The solution was stirred for one hour and the precipitated gabapentin filtered. The crude gabapentin was washed with MTBE and stirred in ethanol to remove traces of benzyl alcohol to obtain pure gabapentin. Yield: 6.9 g (84%), HPLC: 99.6%.

Workup

  1. filtrationThe suspension was filtered
  2. washthe residue washed with about 5 ml benzyl alcohol
  3. addition140 ml of methyl tert.butyl ether (MTBE) was added
  4. stirringThe solution was stirred for one hour
  5. filtrationthe precipitated gabapentin filtered
  6. washThe crude gabapentin was washed with MTBE
  7. stirringstirred in ethanol
  8. customto remove traces of benzyl alcohol

Sources & evidence

ORD record
ord-71757e9d419e4e94ba335e9fa2ca31d5
Source dataset
uspto-grants-2013_04
Patent number
US08431739B2

Reaction notes

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