Fumaric Acid → HCID 19095307, compound

HRID 486565Notes

Reaction equation

HRID 486565 reaction equation
[CH3:1][C:2]1[C:7]2=[CH:8][C:9]3[CH2:10][CH2:11][C:12]4[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=4[C:14]=3[N:6]2[CH2:5][CH2:4][N:3]=1.[BH4-].[Na+].[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25]>C(O)C.O>[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25].[CH3:1][CH:2]1[C:7]2=[CH:8][C:9]3[CH2:10][CH2:11][C:12]4[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=4[C:14]=3[N:6]2[CH2:5][CH2:4][NH:3]1

Participants

6

Reactant 3

HCID 444972Fumaric AcidHCID 4311764Sodium borohydrideHCID 19095284HCID 19095284, compound

Product 1

HCID 19095307HCID 19095307, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

5,6,10,11-Tetrahydro-8-methylbenzo[g]pyrazino[1,2-a]indole (0.6 g) was dissolved in a mixture of 25 ml of ethanol and 2.5 ml of water under argon. The solution was treated portionwise with 0.3 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 50 ml of methylene chloride and washed with 50 ml of 10% ammonia solution. The phases were separated and the aqueous phase was extracted twice with 20 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The crude product, 0.5 g of brown solid, was dissolved in a 20-fold amount of ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 0.2 g (24%) of 5,6,8,9,10,11-hexahydro-8-methylbenzo[g]pyrazino[1,2-a]indole fumarate (1:1); m.pt.: 181°-184° C. (dec.).

Workup

  1. stirringstirred at room temperature overnight
  2. customThereafter, the solvent was removed in a vacuum
  3. washwashed with 50 ml of 10% ammonia solution
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted twice with 20 ml of methylene chloride each time
  6. dry with materialdried with MgSO4
  7. dissolutionThe crude product, 0.5 g of brown solid, was dissolved in a 20-fold amount of ethanol

Sources & evidence

ORD record
ord-dbeb29a497964cbfbe2a42e9b687be54
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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