Sodium Hydroxide → HCID 19095355, compound

HRID 486533Notes

Reaction equation

HRID 486533 reaction equation
[C:1]1([C:7]2[N:8]([CH2:12][CH2:13][NH:14][C:15](=O)[CH3:16])[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29]>O.C(O)C>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29].[CH3:16][C:15]1[C:9]2[N:8]([C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:11][CH:10]=2)[CH2:12][CH2:13][N:14]=1

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 24813Phosphorus oxychlorideHCID 444972Fumaric AcidHCID 19095354HCID 19095354, compound

Product 1

HCID 19095355HCID 19095355, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-[2-(2-Phenylpyrrol-1-yl]-ethyl]acetamide (5.0 g) was added to 30 ml of phosphorus oxychloride under argon and the mixture was boiled under reflux for 1 hour. The cooled mixture was hydrolyzed with 100 ml of 2N sodium hydroxide solution and 230 ml of 28% sodium hydroxide solution (cooling with ice), diluted with 2000 ml of water and extracted with methylene chloride (1×350 ml, 3×200 ml). The organic phases were combined, dried with MgSO4 and freed from solvent. 1.0 g of a total of 4.5 g of crude product was dissolved in a 30-fold amount of ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 0.9 g (57%) of 3,4-dihydro-1-methyl-6-phenylpyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt.: 175° C. (dec.).

Workup

  1. temperatureunder reflux for 1 hour
  2. extractionextracted with methylene chloride (1×350 ml, 3×200 ml)
  3. dry with materialdried with MgSO4
  4. dissolution1.0 g of a total of 4.5 g of crude product was dissolved in a 30-fold amount of ethanol

Sources & evidence

ORD record
ord-21f0dfdc27a24941a0f838c531a1cf51
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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