Fumaric Acid → HCID 19095318, compound

HRID 486593Notes

Reaction equation

HRID 486593 reaction equation
[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]3[C:18]4[N:17]5[CH2:19][CH2:20][N:21]=[C:22]([CH3:23])[C:16]5=[CH:15][C:14]=4[CH2:13][CH2:12][C:11]=3[CH:24]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31]>CO.O.C(O)C>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]3[C:18]4[N:17]5[CH2:19][CH2:20][NH:21][CH:22]([CH3:23])[C:16]5=[CH:15][C:14]=4[CH2:13][CH2:12][C:11]=3[CH:24]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 3

HCID 444972Fumaric AcidHCID 4311764Sodium borohydrideHCID 19095315HCID 19095315, compound

Product 1

HCID 19095318HCID 19095318, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-Cyclohexyl-5,6,10,11-tetrahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole (0.34 g) was dissolved in a mixture of 15 ml of methanol and 1,5 ml of water under argon. The solution was treated portionwise with 0.15 g of sodium borohydride while stirring and stirred at room temperature for 3 hours. Thereafter, the methanol was removed in a vacuum and the residue was stirred with 20 ml of ether and 20 ml of 10% ammonia solution. The phases were separated and the aqueous phase was extracted twice with 20 ml of ether each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The crude product, 0.35 g of colourless 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 (27%) of 3-cyclohexyl-5,6,8,9,10,11-hexahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole fumarate (2:1); m.pt.: 199°-202° C. (dec.).

Workup

  1. stirringstirred at room temperature for 3 hours
  2. customThereafter, the methanol was removed in a vacuum
  3. stirringthe residue was stirred with 20 ml of ether and 20 ml of 10% ammonia solution
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted twice with 20 ml of ether each time
  6. dry with materialdried with MgSO4
  7. dissolutionThe crude product, 0.35 g of colourless oil, was dissolved in a 20-fold amount of ethanol

Sources & evidence

ORD record
ord-f7d8dc7f0aa642b7a56512e5ff85d680
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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