Fumaric Acid → HCID 19095322, compound

HRID 486594Notes

Reaction equation

HRID 486594 reaction equation
[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]2[C:16]3[N:15]4[CH2:17][CH2:18][N:19]=[C:20]([CH3:21])[C:14]4=[CH:13][C:12]=3[CH2:11][CH2:10][C:9]=2[CH:22]=1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+].[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29]>CO.O.C(O)C>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29].[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]2[C:16]3[N:15]4[CH2:17][CH2:18][NH:19][CH:20]([CH3:21])[C:14]4=[CH:13][C:12]=3[CH2:11][CH2:10][C:9]=2[CH:22]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 444972Fumaric AcidHCID 4311764Sodium borohydrideHCID 19095310HCID 19095310, compound

Product 1

HCID 19095322HCID 19095322, compoundYield 19%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-n-Butyl-5,6,10,11-tetrahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole (0.47 g) was dissolved in a mixture of 20 ml of methanol and 2 ml of water under argon. The solution was treated portionwise with 0.18 g of sodium borohydride while stirring and stirred at room temperature for 4 hours. Thereafter, the methanol was removed in a vacuum and the residue was stirred with 50 ml of ether and 20 ml of 10% ammonia solution. The phases were separated and the aqueous phase was extracted once with 50 ml of ether. The organic phases were combined, dried with MgSO4 and freed from solvent. The crude product, 0.47 g of yellowish oil, was dissolved in a 20-fold amount of ethanol and boiled briefly with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 0.11 g (19%) of 3-n-butyl-5,6,8,9,10,11-hexahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole fumarate (2:1); m.pt.: 174°-176° C. (dec.).

Workup

  1. stirringstirred at room temperature for 4 hours
  2. customThereafter, the methanol was removed in a vacuum
  3. stirringthe residue was stirred with 50 ml of ether and 20 ml of 10% ammonia solution
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted once with 50 ml of ether
  6. dry with materialdried with MgSO4
  7. dissolutionThe crude product, 0.47 g of yellowish oil, was dissolved in a 20-fold amount of ethanol

Sources & evidence

ORD record
ord-bc61496b86c4407f9428592ff1b3fa15
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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