Water → HCID 19095341, compound

HRID 486578Notes

Reaction equation

HRID 486578 reaction equation
[C:1]([C:4]1O[C:6]([CH3:15])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)(=O)[CH3:2].[CH2:16]([NH2:19])[CH2:17][NH2:18].O.[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25]>C(O)C>[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25].[CH3:2][C:1]1[C:4]2[N:18]([C:6]([CH3:15])=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:8]=2)[CH2:17][CH2:16][N:19]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 3301EthylenediamineHCID 444972Fumaric AcidHCID 194303131-(5-Methyl-4-phenylfuran-2-yl)ethan-1-one

Product 1

HCID 19095341HCID 19095341, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Acetyl-5-methyl-4-phenylfuran (1.9 g) was heated to 150° C. for 1 hour under argon with 6.3 ml of 1,2-ethanediamine and 0.6 ml of water. After cooling the mixture was poured into 500 ml of water and the mixture was extracted three times with 80 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 1.9 g of brown oil, was chromatographed on 100 g of aluminium oxide (neutral, III) with methylene chloride as the eluent. 0.6 g of a total of 1.2 g (56%) of crude product were dissolved in a 20-fold amount of ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 0.4 g of 3,4-dihydro-1,6-dimethyl-7-phenylpyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt: 180°-182° C. (dec.).

Workup

  1. temperatureAfter cooling the mixture
  2. extractionthe mixture was extracted three times with 80 ml of methylene chloride each time
  3. dry with materialdried with MgSO4
  4. customThe residue, 1.9 g of brown oil, was chromatographed on 100 g of aluminium oxide (neutral, III) with methylene chloride as the eluent
  5. dissolution0.6 g of a total of 1.2 g (56%) of crude product were dissolved in a 20-fold amount of ethanol

Sources & evidence

ORD record
ord-34c2521a85e74449b0f8c210d61e762d
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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