Pyridine → 3-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-amine

HRID 1774308

Reaktionsgleichung

Reaktionsgleichung von HRID 1774308
[CH3:1][CH:2]([CH2:4][CH:5]1[C:18](=O)[CH2:17][CH:16]2[N:7]([CH2:8][CH2:9][C:10]3[C:15]2=[CH:14][C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=3)[CH2:6]1)[CH3:3].Cl.NO.[N:27]1C=CC=CC=1>C(O)C>[CH2:4]([CH:5]1[CH2:6][N:7]2[CH2:8][CH2:9][C:10]3[C:15]([CH:16]2[CH2:17][CH:18]1[NH2:27])=[CH:14][C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=3)[CH:2]([CH3:3])[CH3:1]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6018TetrabenazineHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 120874003-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

HG-6 was also synthesized using the following alternative method: tetrabenazine (317 mg, 1 mmol) was dissolved in ethanol (EtOH, 10 ml) and hydroxylamine hydrochloride (70 mg, 1 mmol) was added, followed by the addition of pyridine (1 ml). The reaction was refluxed for 2 hours. After removing solvent, the residue was redissolved in methanol (MeOH, 10 ml). To this solution, MoO3 (80 mg) and sodium borohydride (80 mg) were slowly added. The reaction was stirred at room temperature for 24 hours and quenched with water. The aqueous solution was extracted with methylene chloride (10 ml) twice. The combined organic phase was washed with brine and dried with sodium sulfate. After removing solvent, the residue was purified by chromatography. Two hundred and fifty milligrams of HG-6 (3-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-amine) was obtained as white solid (yield: 78%).

Aufarbeitung

  1. customHG-6 was also synthesized
  2. temperatureThe reaction was refluxed for 2 hours
  3. customAfter removing solvent
  4. dissolutionthe residue was redissolved in methanol (MeOH, 10 ml)
  5. additionTo this solution, MoO3 (80 mg) and sodium borohydride (80 mg) were slowly added
  6. customquenched with water
  7. extractionThe aqueous solution was extracted with methylene chloride (10 ml) twice
  8. washThe combined organic phase was washed with brine
  9. dry with materialdried with sodium sulfate
  10. customAfter removing solvent
  11. customthe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f9b9c621464d4997805824616a9d5882
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260391B2

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