Sodium Hydroxide → HCID 19095283, compound

HRID 486535Notes

Reaction equation

HRID 486535 reaction equation
[N:1]1([CH2:14][CH2:15][NH:16][C:17](=O)[CH3:18])[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[CH2:6][CH2:5][C:4]=2[CH:3]=[CH:2]1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31]>O.C(O)C>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[CH3:18][C:17]1[C:2]2=[CH:3][C:4]3[CH2:5][CH2:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[N:1]2[CH2:14][CH2:15][N:16]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 444972Fumaric AcidHCID 19095320HCID 19095320, compound

Product 1

HCID 19095283HCID 19095283, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-[2-(4,5-Dihydro-1H-benzo[g]indol-1-yl]ethyl]-acetamide (5.3 g) was stirred with 60 ml of phosphorus oxychloride at room temperature for 1 hour. The reaction mixture was hydrolyzed at 0° C. with 500 ml of 28% sodium hydroxide solution, diluted with 4000 ml of water and extracted three times with 300 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. 2.0 g of a total of 5.0 g of crude product were dissolved in a 30-fold amount of ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There were obtained 2.3 g (67%) of 5,6,10,11-tetrahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole fumarate (2:3); m.pt.: 181° C. (dec.).

Workup

  1. extractionextracted three times with 300 ml of methylene chloride each time
  2. dry with materialdried with MgSO4
  3. dissolution2.0 g of a total of 5.0 g of crude product were dissolved in a 30-fold amount of ethanol

Sources & evidence

ORD record
ord-4716888c7ffb454cb6397b14554fd1a7
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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