Ethylene Oxide → Gabapentin

HRID 1790872Notes

Reaction equation

HRID 1790872 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.C1OC1>C(O)CCC>[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 6354Ethylene OxideHCID 6453919Gabapentin hydrochloride

Product 1

HCID 3446GabapentinYield 77.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
-5 °C

Procedure

Gabapentin hydrochloride (72 mmol) was suspended in 50 mL of n-butanol and heated gently until complete dissolution. The solution was cooled below 110° C. and ethylene oxide (144 mmol) was added in one portion. The mixture was stirred for 16 hours below 10° C., after which it was cooled to −5° C. Pure gabapentin was recovered by filtration and washed with cold isopropanol. Drying at 40–50° C. under reduced pressure afforded 9.6 g of pure gabapentin. Same as Example 2, but ethylene was used instead of propylene oxide 9.6 g were recovered.

Workup

  1. temperatureheated gently until complete dissolution
  2. temperatureThe solution was cooled below 110° C.
  3. filtrationPure gabapentin was recovered by filtration
  4. washwashed with cold isopropanol
  5. customDrying at 40–50° C. under reduced pressure

Sources & evidence

ORD record
ord-f65092b4471e4eac9815f0dc7e6142f9
Source dataset
uspto-grants-2006_07
Patent number
US07071356B1

Reaction notes

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