Ammonia → Gabapentin

HRID 974437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 974437
N.Cl.[NH2:3][CH2:4][C:5]1([CH2:11][C:12]([OH:14])=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>O>[NH2:3][CH2:4][C:5]1([CH2:11][C:12]([OH:14])=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 6453919Gabapentin hydrochloride

Produkt 1

HCID 3446GabapentinAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A 3 m long and 20 mm wide chromatography column is filled with 50 1 of an ion exchanger resin (IRA 68). The resin is regenerated with a solution of 14 l concentrated aqueous ammonia in 300 l demineralized water and subsequently washed with 150 l demineralized water. As soon as the eluate has reached pH 6.8 and no more chloride can be detected, a solution of 8.67 kg (40.8 mole) 1-aminomethyl-1-cyclohexaneacetic acid hydrochloride in 43 l demineralized water is added to the column. The free amino acid is eluted with demineralized water at a rate of 1.5 l/min and collected in 15 fractions of 15 1. The combined fractions are evaporated at 6.65 Pa and at most 45° C. The solid white residue is introduced into 20 l methanol, heated to reflux, filtered and cooled to - 10° C. The product which crystallizes out is centrifuged off, washed with 10 1 cold methanol and dried for 17 hours at 30-40° C. 4.9 kg (71% of theory) of pure 1-(aminomethyl)-cyclohexaneacetic acid are obtained; m.p. 165° C. A further 0.8 kg can be obtained by working up the mother liquors.

Aufarbeitung

  1. additionA 3 m long and 20 mm wide chromatography column is filled with 50 1 of an ion exchanger resin (IRA 68)
  2. washsubsequently washed with 150 l
  3. additionis added to the column
  4. washThe free amino acid is eluted with demineralized water at a rate of 1.5 l/min
  5. customcollected in 15 fractions of 15 1
  6. customThe combined fractions are evaporated at 6.65 Pa and at most 45° C
  7. additionThe solid white residue is introduced into 20 l methanol
  8. temperatureheated
  9. temperatureto reflux
  10. filtrationfiltered
  11. customThe product which crystallizes out
  12. washwashed with 10 1 cold methanol
  13. customdried for 17 hours at 30-40° C

Quellen und Nachweise

ORD-Eintrag
ord-42f9a6bdccef4ecc97193f758d8ea3f0
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05068413

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