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

HRID 864031
Notes
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Reaction equation

HRID 864031 reaction equation
[N:1]([CH:4]([CH3:20])[CH2:5][N:6]1[C:10]2=[CH:11][C:12]3[C:17]([CH2:16][CH:15]=[CH:14][C:13]=3[O:18][CH3:19])=[C:9]2[CH:8]=[N:7]1)=[N+]=[N-].[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25]>C(O)C.C(OCC)C.CO.[Pt]=O>[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25].[CH3:19][O: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])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 444972Fumaric AcidHCID 19420926HCID 19420926, compound

Product 1

HCID 19420934(RS)-2-(7-methoxy-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarateYield 78.3%

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent
HCID 887
Methanol
Solvent
HCID 3283Diethyl EtherSolvent

Procedure

0.85 g (3.2 mmol) of (RS)-1-(2-azido-propyl)-7-methoxy-1,4-dihydro-indeno[2,1-c]pyrazole dissolved in 50 ml of anhydrous ethanol was hydrogenated on 85 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 70 ml of anhydrous diethyl ether, filtered and treated while stirring with a solution of 371 mg (3.2 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. 0.9 g (78%) of (RS)-2-(7-methoxy-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarate (1:1) with m.p. 182° was obtained.

Workup

  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

Sources & evidence

ORD record
ord-d375a6ff4d1d41bc95ed8e7657c1f630
Source dataset
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05561150

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes