Fumaric Acid → (RS)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indazol-1-yl)-1-methyl-ethylamine fumarate

HRID 864067Notes

Reaction equation

HRID 864067 reaction equation
[N:1]([CH:4]([CH3:21])[CH2:5][N:6]1[C:14]2[C:13]3[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:12]=3[CH2:11][CH2:10][C:9]=2[CH:8]=[N:7]1)=[N+]=[N-].[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26]>C(O)C.C(OCC)C.CO.[Pt]=O>[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26].[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:12]2[CH2:11][CH2:10][C:9]3[CH:8]=[N:7][N:6]([CH2:5][CH:4]([NH2:1])[CH3:21])[C:14]=3[C:13]=2[CH:15]=1

Participants

7

Reactant 2

HCID 444972Fumaric AcidHCID 19420918(RS)-1-(2-azido-propyl)-4,5-dihydro-8-methoxy-1H-benz[g]indazole

Product 1

HCID 19420940(RS)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indazol-1-yl)-1-methyl-ethylamine fumarateYield 75%

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1 g (3.5 mmol) of (RS)-1-(2-azido-propyl)-4,5-dihydro-8-methoxy-1H-benz[g]indazole dissolved in 50 ml of anhydrous ethanol was hydrogenated over 100 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 406 mg (3.5 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. 0.98 g (75%) of (RS)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indazol-1-yl)-1-methyl-ethylamine fumarate (1:1) with m.p. 174°-176° 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-54984ddc077a474db45cfefe3287d830
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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