Fumaric Acid → HCID 19095424, compound

HRID 486566Notes

Reaction equation

HRID 486566 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:13]3[N:12]4[CH2:14][CH2:15][N:16]=[C:17]([CH3:18])[C:11]4=[CH:10][C:9]=3[CH2:8][CH2:7][C:6]=2[CH:19]=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].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:13]3[N:12]4[CH2:14][CH2:15][NH:16][CH:17]([CH3:18])[C:11]4=[CH:10][C:9]=3[CH2:8][CH2:7][C:6]=2[CH:19]=1

Participants

7

Reactant 3

HCID 444972Fumaric AcidHCID 4311764Sodium borohydrideHCID 19095382HCID 19095382, compound

Product 1

HCID 19095424HCID 19095424, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-Chloro-5,6,10,11-tetrahydro-8-methylbenzo[g]pyrazino[1,2-a]indole (0.9 g) was dissolved in a mixture of 40 ml of methanol and 4 ml of water under argon. The solution was treated portionwise with 0.4 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 30 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The crude product, 0.9 g of orange solid, was dissolved in a 40-fold amount of hot ethanol and treated while hot with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 1.0 g (78%) of 3-chloro-5,6,8,9,10,11-hexahydro-8-methylbenzo[g]pyrazino[1,2-a]indole fumarate (1:1); m.pt.: 202°- 203° 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 30 ml of methylene chloride each time
  6. dry with materialdried with MgSO4
  7. dissolutionThe crude product, 0.9 g of orange solid, was dissolved in a 40-fold amount of hot ethanol

Sources & evidence

ORD record
ord-69aad42e1e61403eaef247dac02302e3
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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