Fumaric Acid → HCID 19095426, compound

HRID 486567Notes

Reaction equation

HRID 486567 reaction equation
[CH3:1][CH:2]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]2[N:7]3[CH2:15][CH2:16][N:17]=[C:18]([CH3:19])[C:6]3=[CH:5][C:4]=2[CH2:3]1.[BH4-].[Na+].[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26]>CO.O.C(O)C>[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26].[CH3:1][CH:2]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]2[N:7]3[CH2:15][CH2:16][NH:17][CH:18]([CH3:19])[C:6]3=[CH:5][C:4]=2[CH2:3]1

Participants

7

Reactant 3

HCID 444972Fumaric AcidHCID 4311764Sodium borohydrideHCID 19095291HCID 19095291, compound

Product 1

HCID 19095426HCID 19095426, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5,6,10,11-Tetrahydro-5,8-dimethylbenzo[g]pyrazino[1,2-a]indole (2.0 g) was dissolved in a mixture of 80 ml of methanol and 8 ml of water under argon. The solution was treated portionwise with 0.9 g of sodium borohydride while stirring and stirred at room temperature overnight. Thereafter, the solvent was removed in a vacuum, the residue was taken up in 100 ml of methylene chloride and washed with 100 ml of 10% ammonia solution. The phases were separated and the aqueous phase was extracted twice with 50 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The crude product, 2.0 g of yellow-brown oil, was dissolved in a 25-fold amount of hot ethanol and treated with 1.1 equivalents of a hot saturated solution of fumaric acid in ethanol. There were obtained 2.4 g (81%) of 5,6,8,9,10,11-hexahydro-5,8-dimethylbenzo[g]pyrazino[1,2-a]indole fumarate (1:1); m.pt.: 196°-199° C.

Workup

  1. stirringstirred at room temperature overnight
  2. customThereafter, the solvent was removed in a vacuum
  3. washwashed with 100 ml of 10% ammonia solution
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted twice with 50 ml of methylene chloride each time
  6. dry with materialdried with MgSO4
  7. dissolutionThe crude product, 2.0 g of yellow-brown oil, was dissolved in a 25-fold amount of hot ethanol

Sources & evidence

ORD record
ord-f6e4467039164546ada889d4dfdd78ce
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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