Water → HCID 19095327, compound

HRID 486569Notes

Reaction equation

HRID 486569 reaction equation
[I-].[CH3:2][C:3]1[C:4]2[N:5]([C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][CH:12]=2)[CH2:6][CH2:7][N+:8]=1[CH3:9].O.[BH4-].[Na+].[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26]>CO.C(O)C>[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26].[CH3:2][CH:3]1[N:8]([CH3:9])[CH2:7][CH2:6][N:5]2[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][CH:12]=[C:4]12

Participants

7

Reactant 4

HCID 962WaterHCID 444972Fumaric AcidHCID 4311764Sodium borohydrideHCID 19095281HCID 19095281, compound

Product 1

HCID 19095327HCID 19095327, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

3,4-Dihydro-1,2-dimethyl-6-phenylpyrrolo[1,2-a]pyrazinium iodide (0.4 g) was dissolved in 20 ml of methanol and 0.5 ml of water under argon and, after the addition of 0.2 g of sodium borohydride, stirred at room temperature for 15 minutes. The methanol was removed in a vacuum and the residue was stirred briefly with 50 ml of methylene chloride and 20 ml of 10% ammonia solution. The aqueous phase was extracted twice with 20 ml of methylene chloride each time, the organic phases were combined, dried with MgSO4 and freed from solvent. The crude product, 0.2 g of yellow oil, was taken up in a 25-fold amount of ethanol, treated with 2 equivalents of a saturated solution of fumaric acid in ethanol, concentrated to 2 ml and boiled with 5 ml of ethyl acetate. There was obtained 0.2 g (51%) of 1,2,3,4-tetrahydro-1,2-dimethyl-6-phenylpyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt. 127° -128° C. (dec.).

Workup

  1. customThe methanol was removed in a vacuum
  2. stirringthe residue was stirred briefly with 50 ml of methylene chloride and 20 ml of 10% ammonia solution
  3. extractionThe aqueous phase was extracted twice with 20 ml of methylene chloride each time
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated to 2 ml

Sources & evidence

ORD record
ord-6eee7dc2ebc94331a1f6d3fb79657c77
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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