Fumaric Acid → HCID 19095351, compound

HRID 486562Notes

Reaction equation

HRID 486562 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[CH2:14][CH2:15][N:16]=[C:17]([CH3:18])[C:12]3=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[BH4-].[Na+].[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25]>CO.O.C(O)C>[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[CH2:14][CH2:15][NH:16][CH:17]([CH3:18])[C:12]3=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 3

HCID 444972Fumaric AcidHCID 4311764Sodium borohydrideHCID 19095348HCID 19095348, compound

Product 1

HCID 19095351HCID 19095351, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

6-(3,4-Dichlorophenyl)-3,4-dihydro-1-methylpyrrolo[1,2-a]pyrazine (1.8 g) was dissolved in a mixture of 100 ml of methanol and 10 ml of water under argon. The solution was treated portionwise with 0.7 g of sodium borohydride while stirring and stirred at room temperature overnight. Thereafter, the methanol was removed in a vacuum, the residue was taken up in 150 ml of methylene chloride and washed with 65 ml of 10% ammonia solution. The phases were separated and the aqueous phase was extracted twice with 70 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The crude product, 1.8 g of brown oil, 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 were obtained 2.0 g (92%) of 6-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-methylpyrrolo[1,2-a]pyrazine fumarate (2:1); m.pt.: 224°-226° C. (dec.).

Workup

  1. stirringstirred at room temperature overnight
  2. customThereafter, the methanol was removed in a vacuum
  3. washwashed with 65 ml of 10% ammonia solution
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted twice with 70 ml of methylene chloride each time
  6. dry with materialdried with MgSO4
  7. dissolutionThe crude product, 1.8 g of brown oil, was dissolved in a 20-fold amount of ethanol

Sources & evidence

ORD record
ord-3e34368cbbf64308977930de17b1d44e
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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