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Fumaric Acid → (RS)-2-(7-methyl-1,4-dihydroindeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarate

HRID 864054
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 864054
[N:1]([CH:4]([CH3:19])[CH2:5][N:6]1[C:10]2=[CH:11][C:12]3[C:17]([CH2:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[C:9]2[CH:8]=[N:7]1)=[N+]=[N-].[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24]>C(O)C.C(OCC)C.CO.[Pt]=O>[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24].[CH3:18][C:13]1[CH:14]=[CH:15][CH2:16][C:17]2[C:12]=1[CH:11]=[C:10]1[C:9]=2[CH:8]=[N:7][N:6]1[CH2:5][CH:4]([NH2:1])[CH3:19]
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Komponenten

7

Edukt 2

HCID 444972Fumaric AcidHCID 19420941(RS)-1-(2-azido-propyl)-7-methyl-1,4-dihydro-indeno[2,1-c]pyrazole

Produkt 1

HCID 19420924(RS)-2-(7-methyl-1,4-dihydroindeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 82844Platinum oxide (PtO)KatalysatorHCID 702
Ethanol
Lösungsmittel
HCID 887MethanolLösungsmittel
HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

1.38 g (5.45 mmol) of (RS)-1-(2-azido-propyl)-7-methyl-1,4-dihydro-indeno[2,1-c]pyrazole dissolved in 60 ml of anhydrous ethanol were hydrogenated over 140 mg of platinum oxide for 2 hours. The catalyst was subsequently filtered off, rinsed with ethanol and the solvent was removed in a vacuum. The colorless oil obtained was dissolved in 80 ml of anhydrous diethyl ether, filtered and treated while stirring with a solution of 633 mg (5.45 mmol) of fumaric acid in 10 ml of methanol. The mixture was stirred at room temperature for 15 hours and the white crystals were subsequently filtered off. 1.62 g (87%) of (RS)-2-(7-methyl-1,4-dihydroindeno[2,1-c]pyrazol-1-yl )-1-methyl-ethylamine fumarate (1:1) with m.p. 205° were obtained.

Aufarbeitung

  1. filtrationThe catalyst was subsequently filtered off
  2. washrinsed with ethanol
  3. customthe solvent was removed in a vacuum
  4. customThe colorless oil obtained
  5. filtrationfiltered
  6. additiontreated
  7. filtrationthe white crystals were subsequently filtered off

Quellen und Nachweise

ORD-Eintrag
ord-300ed05ed177423382dc0d31a14f2175
Quelldatensatz
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05561150

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