Gabapentin → Prop-2-enyl 2-[1-(aminomethyl)cyclohexyl]acetate;hydrochloride

HRID 30515

Reaktionsgleichung

Reaktionsgleichung von HRID 30515
[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.[CH2:13](O)[CH:14]=[CH2:15].S(Cl)([Cl:19])=O>C(OCC)C>[ClH:19].[NH2:12][CH2:11][C:4]1([CH2:7][C:8]([O:10][CH2:15][CH:14]=[CH2:13])=[O:9])[CH2:3][CH2:2][CH2:1][CH2:6][CH2:5]1

Komponenten

5

Edukt 3

HCID 3446GabapentinHCID 7858Allyl AlcoholHCID 24386Thionyl Chloride

Produkt 1

HCID 66743418Prop-2-enyl 2-[1-(aminomethyl)cyclohexyl]acetate;hydrochlorideAusbeute 88,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A dry 500 mL, three-neck, round-bottomed flask was fitted with a magnetic stirring bar and a 100 mL pressure-equalizing addition funnel and flushed with nitrogen gas. The flask was charged with gabapentin (17.1 g, 0.1 mol) and allyl alcohol (100 mL, 1.46 mol) and the entire mixture was cooled to 0° C. in an ice-water bath. Thionyl chloride (22.5 mL, 36 g, 0.3 mol) was added drop-wise over a period of 30 min to the stirred solution, and the reaction mixture allowed to stir for 16 h at room temperature. The mixture was then diluted with diethyl ether (200 mL) and cooled to 0° C. while stirring. After several minutes white crystals formed, and were collected by filtration. The crude compound was recrystallized from a mixture of ethanol and diethyl ether (50 mL: 150 mL) to give the product (13) as a white solid (22 g, 88% yield), m.p: 138-142° C. 1H NMR (CD3OD, 400 MHz): δ 1.36-1.54 (m, 10H), 2.57 (s, 2H), 3.05 (s, 2H), 4.61 (d, 2H), 5.22 (dd, 1H), 5.33 (dd, 1H), 5.90-6.00 (m, 1H). MS (ESI) m/z 212.0 (M+H+).

Aufarbeitung

  1. customA dry 500 mL, three-neck, round-bottomed flask was fitted with a magnetic stirring bar and a 100 mL pressure-equalizing addition funnel
  2. customflushed with nitrogen gas
  3. temperaturecooled to 0° C.
  4. stirringwhile stirring
  5. customAfter several minutes white crystals formed
  6. filtrationwere collected by filtration
  7. customThe crude compound was recrystallized from a mixture of ethanol and diethyl ether (50 mL: 150 mL)

Quellen und Nachweise

ORD-Eintrag
ord-82e707b05926446ba4ee960a9601be13
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423169B2

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