Sodium Hydroxide → 6-(1,3-Benzodioxol-5-yl)-3,4-dihydro-1-methylpyrrolo[1,2-a]pyrazine fumarate

HRID 486529Notes

Reaction equation

HRID 486529 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:11]([CH2:15][CH2:16][NH:17][C:18](=O)[CH3:19])[CH:12]=[CH:13][CH:14]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>O.C(O)C>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:11]4[CH2:15][CH2:16][N:17]=[C:18]([CH3:19])[C:12]4=[CH:13][CH:14]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 24813Phosphorus oxychlorideHCID 444972Fumaric AcidHCID 19095413HCID 19095413, compound

Product 1

HCID 190954176-(1,3-Benzodioxol-5-yl)-3,4-dihydro-1-methylpyrrolo[1,2-a]pyrazine fumarateYield 66%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-[2-[2-(1,3-Benzodioxol-5-yl)-pyrrol-1-yl]-ethyl]acetamide (1.7 g) was treated with 10 ml of phosphorus oxychloride under argon and boiled for 45 minutes while stirring. The reaction mixture was hydrolyzed at 0° C. with 50 ml of 2N sodium hydroxide solution and 50 ml of 28% sodium hydroxide solution, diluted with 600 ml of water and extracted with methylene chloride (1×100 ml, 2×60 ml). The organic extracts were combined, dried with MgSO4 and freed from solvent. 1.4 g of crude product was dissolved in a 20-fold amount of ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There were obtained 1.5 g (66%) of 6-(1,3-benzodioxol-5-yl)-3,4-dihydro-1-methylpyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt.: 191°-193° C. (dec.).

Workup

  1. extractionextracted with methylene chloride (1×100 ml, 2×60 ml)
  2. dry with materialdried with MgSO4
  3. dissolution1.4 g of crude product was dissolved in a 20-fold amount of ethanol

Sources & evidence

ORD record
ord-60e593cdb5244d4bac805a48834385f5
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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