Sodium Hydroxide → HCID 19095438, compound

HRID 486532Notes

Reaction equation

HRID 486532 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:12]([CH2:16][CH2:17][NH:18][C:19](=O)[CH3:20])[CH:13]=[CH:14][CH:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33]>O.C(O)C>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:12]3[CH2:16][CH2:17][N:18]=[C:19]([CH3:20])[C:13]3=[CH:14][CH:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 24813Phosphorus oxychlorideHCID 444972Fumaric AcidHCID 19095412HCID 19095412, compound

Product 1

HCID 19095438HCID 19095438, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-[2-[2-(3,4-Dimethoxyphenyl)pyrrol-1-yl]-ethyl]-acetamide (2.6 g) was treated with 20 ml of phosphorus oxychloride under argon and boiled for 1 hour while stirring. The reaction mixture was hydrolyzed at 0° C. with 100 ml of 2N sodium hydroxide solution and 100 ml of 28% sodium hydroxide solution, diluted with 1200 ml of water and extracted with methylene chloride (1×200 ml, 2×100 ml). The organic extracts were combined, dried with MgSO4 and freed from solvent. 1.4 g of a total of 2.7 g of crude product were chromatographed on 30 g of silica gel with methylene chloride/methanol (19:1) as the eluent. The product, 0.8 g of brown oil, was dissolved in a 40-fold amount of ethanol, treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol and concentrated to a volume of 10 ml. There was obtained 0.8 g of 6-(3,4-dimethoxyphenyl)-3,4-dihydro-1-methylpyrrolo[1,2-a]pyrazine fumarate (1:1.3); m.pt.: 158°-160° C. (dec.). A sample was recrystallized from a 40-fold amount of ethanol and yielded the (1:1) fumarate which melted at 160°-161° C. with decomposition.

Workup

  1. extractionextracted with methylene chloride (1×200 ml, 2×100 ml)
  2. dry with materialdried with MgSO4
  3. custom1.4 g of a total of 2.7 g of crude product were chromatographed on 30 g of silica gel with methylene chloride/methanol (19:1) as the eluent
  4. dissolutionThe product, 0.8 g of brown oil, was dissolved in a 40-fold amount of ethanol
  5. concentrationconcentrated to a volume of 10 ml

Sources & evidence

ORD record
ord-a8c23c7ca22d44ec85e5b2e9a302fd2b
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

Loading…