Formaldehyde → HCID 19095288, compound

HRID 486552Notes

Reaction equation

HRID 486552 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C=O.[C:17]([OH:24])(=[O:23])/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21]>C(O)(=O)C.C(O)C>[C:17]([OH:24])(=[O:23])/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21].[C:9]1([C:5]2[N:4]3[CH2:3][CH2:2][NH:1][CH2:17][C:8]3=[CH:7][CH:6]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 444972Fumaric AcidHCID 19095276HCID 19095276, compound

Product 1

HCID 19095288HCID 19095288, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

Crude 1-(2-aminoethyl)-2-phenylpyrrole (0.3 g) was dissolved in 5 ml of acetic acid under argon and treated with 0.1 ml of a 36.5% aqueous formaldehyde solution. The reaction mixture was stirred at room temperature for 64 hours and subsequently concentrated in a vacuum. The residue was stirred briefly with 50 ml of methylene chloride and 20 ml of 10% ammonia solution. The phases were separated, the organic phase was dried with MgSO4 and freed from solvent. The residue, 0.4 g of yellow oil, was chromatographed on 70 g of silica gel with methylene chloride/methanol (49:1) as the eluent. The product, 0.3 g of yellow oil, was taken up in a 20-fold amount of ethanol and treated with 2 equivalents of a saturated solution of fumaric acid in ethanol. The separated crystals were recrystallized from ethanol. There was obtained 0.2 g (40%) of 1,2,3,4-tetrahydro-6-phenylpyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt.: 182°- 184° C. (dec.).

Workup

  1. concentrationsubsequently concentrated in a vacuum
  2. stirringThe residue was stirred briefly with 50 ml of methylene chloride and 20 ml of 10% ammonia solution
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried with MgSO4
  5. customThe residue, 0.4 g of yellow oil, was chromatographed on 70 g of silica gel with methylene chloride/methanol (49:1) as the eluent
  6. customThe separated crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-189aef885c49496db04af39d6e13320f
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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