Formaldehyde → HCID 19095396, compound

HRID 486554Notes

Reaction equation

HRID 486554 reaction equation
C=O.[NH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7]1.[C:19]([OH:26])(=[O:25])/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23].CO>C(O)C>[C:19]([OH:26])(=[O:25])/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23].[CH:15]1[C:13]2[C:14]3[N:6]4[CH2:5][CH2:4][NH:3][CH2:19][C:7]4=[CH:8][C:9]=3[CH2:10][CH2:11][C:12]=2[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 444972Fumaric AcidHCID 19095420HCID 19095420, compound

Product 1

HCID 19095396HCID 19095396, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

36% aqueous formaldehyde solution (1.4 ml) was added under argon to a solution of 3.7 g of 1-(2-aminoethyl)-4,5-dihydro-1H-benzo[g]indole in 70 ml of ethanol. The reaction solution was stirred under reflux for 2 hours, subsequently cooled and freed from solvent. The residue was chromatographed on 250 g of silica gel with methylene chloride/methanol (49:1) as the eluent. 1.3 g of a total of 2.8 g of product were dissolved in a 20-fold amount of hot ethanol and treated while hot with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. The precipitated solid was boiled in a 150-fold amount of methanol, filtered while hot and concentrated to a 60-fold amount of solvent. There were obtained 1.2 g (53%) of 5,6,8,9,10,11-hexahydrobenzo[g]pyrazino[1,2-a]indole fumarate (2:1); m.pt.: 183°-184° C. (dec.).

Workup

  1. temperatureunder reflux for 2 hours
  2. temperaturesubsequently cooled
  3. customThe residue was chromatographed on 250 g of silica gel with methylene chloride/methanol (49:1) as the eluent
  4. dissolution1.3 g of a total of 2.8 g of product were dissolved in a 20-fold amount of hot ethanol
  5. filtrationfiltered while hot and
  6. concentrationconcentrated to a 60-fold amount of solvent

Sources & evidence

ORD record
ord-b071cfea490e4f77807acd634846db3f
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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