Fumaric Acid → HCID 19095286, compound

HRID 486558Notes

Reaction equation

HRID 486558 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]3[CH2:13][CH2:14][N:15]=[C:16]([CH3:17])[C:11]3=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+].[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24]>CO.O.C(O)C>[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]3[CH2:13][CH2:14][NH:15][CH:16]([CH3:17])[C:11]3=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 444972Fumaric AcidHCID 4311764Sodium borohydrideHCID 19095297HCID 19095297, compound

Product 1

HCID 19095286HCID 19095286, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

6-(m-Chlorophenyl)-3,4-dihydro-1-methylpyrrolo[1,2-a]pyrazine (2.0 g) was dissolved in a mixture of 100 ml of methanol and 10 ml of water under argon. The solution was treated portionwise with 0.9 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 50 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, 2.0 g of yellow 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. The solution was concentrated to 10 ml and boiled briefly with 100 ml of ethyl acetate. There were obtained 1.7 g (57%) of 6-(m-chlorophenyl)-1,2,3,4-tetrahydro-1 -methylpyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt.: 165°-167° C. (dec.).

Workup

  1. stirringstirred at room temperature overnight
  2. customThereafter, the methanol 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 70 ml of methylene chloride each time
  6. dry with materialdried with MgSO4
  7. dissolutionThe crude product, 2.0 g of yellow oil, was dissolved in a 20-fold amount of ethanol
  8. concentrationThe solution was concentrated to 10 ml

Sources & evidence

ORD record
ord-5c8e3a03d3564a53a8417e61016a23c6
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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