Gabapentin hydrochloride → Gabapentin
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>C(O)(C)C>[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]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
In this Example, gabapentin hydrochloride was dissolved in 130 ml of dry isopropanol at 25° C. Then 1.1 grams of active carbon was added and the suspension was heated to 40° C. and maintained at this temperature for 2 hours. The suspension was filtered at 40° C. and the filter cake was then washed twice, each time with an additional 15 ml of isopropanol. The washings were added to the already separated solution of gabapentin hydrochloride in isopropanol. After half an hour of mixing at 25° C., 19.5 grams of tributylamine was added during half an hour and the mixing was continued for two hours at the same temperature. The formed gabapentin base was separated from the suspension by filtration and washed with 23 ml of methanol to give gabapentin crude. After reslurry as in Example 1B gabapentin pure was obtained at a yield of 58.8% and chloride anion content of 7 ppm Cl−.
Workup
- additionThen 1.1 grams of active carbon was added
- temperaturemaintained at this temperature for 2 hours
- filtrationThe suspension was filtered at 40° C.
- washthe filter cake was then washed twice
- additionThe washings were added to the already separated solution of gabapentin hydrochloride in isopropanol
- additionAfter half an hour of mixing at 25° C.
- addition19.5 grams of tributylamine was added during half an hour
- customThe formed gabapentin base was separated from the suspension by filtration
- washwashed with 23 ml of methanol
Sources & evidence
- ORD record
- ord-c8598b15ddfa41c08c4519ec94850dac
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06531509B2
Reaction notes
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