Water → 3,4-Dihydro-1-methyl-7-phenylpyrrolo[1,2-a]pyrazine fumarate

HRID 486556Notes

Reaction equation

HRID 486556 reaction equation
[C:1]([C:4]1O[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)(=O)[CH3:2].[CH2:15]([NH2:18])[CH2:16][NH2:17].O.[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24]>C(O)C>[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24].[CH3:2][C:1]1[C:4]2[N:17]([CH:6]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:8]=2)[CH2:16][CH2:15][N:18]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 3301EthylenediamineHCID 444972Fumaric AcidHCID 190954162-Acetyl-4-phenylfuran

Product 1

HCID 190953303,4-Dihydro-1-methyl-7-phenylpyrrolo[1,2-a]pyrazine fumarateYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Acetyl-4-phenylfuran (0.7 g) was heated at 100° C. for 1 hour under argon with 0.8 ml of 1,2-ethanediamine and 0.1 ml of water. After cooling 50 ml of water were added and the mixture was extracted three times with 50 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 0.7 g of brown oil, was chromatographed on 60 g of silica gel with methylene chloride/methanol (19:1) as the eluent. The crude product, 0.4 g of brown solid, was dissolved in a 50-fold amount of hot ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 0.4 g (31%) of 3,4-dihydro-1-methyl-7-phenylpyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt.: 181° C. (dec.)

Workup

  1. additionwere added
  2. extractionthe mixture was extracted three times with 50 ml of methylene chloride each time
  3. dry with materialdried with MgSO4
  4. customThe residue, 0.7 g of brown oil, was chromatographed on 60 g of silica gel with methylene chloride/methanol (19:1) as the eluent
  5. dissolutionThe crude product, 0.4 g of brown solid, was dissolved in a 50-fold amount of hot ethanol

Sources & evidence

ORD record
ord-6ddccc03a1ba4de7b1538a4808e1bee9
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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