Acetonitrile → HCID 54159930, compound

HRID 486784Notes

Reaction equation

HRID 486784 reaction equation
[NH2:1][C@@H:2]1[CH2:22][C@H:6]2[CH2:7][N:8]([C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]3[CH:10]=[CH:11][C:12]([Br:13])=[C:4]([C:5]=32)[CH2:3]1.[C:23]([O-])([O-])=O.[K+].[K+].[CH2:29](I)[CH2:30][CH3:31].[CH3:33][C:34]#N>>[C:14]([N:8]1[C:9]2[CH:10]=[CH:11][C:12]([Br:13])=[C:4]3[CH2:3][C@H:2]([N:1]([CH2:23][CH2:34][CH3:33])[CH2:29][CH2:30][CH3:31])[CH2:22][C@H:6]([C:5]=23)[CH2:7]1)(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 53876427HCID 53876427, compound

Product 1

HCID 54159930HCID 54159930, compound

Procedure

A reaction mixture of (2aR,4R)-4-amino-1-benzoyl-6-bromo-1,2,2a,3,4,5-hexahydrobenz[cd]indole (6.8 g, 0.019 mol), K2CO3 (8.28 g, 0.06 mol) and n-propyliodide (10.2 g, 0.06 mol) in 200 mL of CH3CN was stirred at reflux temperature for 16 h. The reaction mixture was filtered and solvent was evaporated. The residue was dissolved in EtOAc and the solution was extracted with dilute HCl. The acidic solution was made alkaline with concentrated NH4OH. The basic mixture was extracted with EtOAc. The organic solution was washed with brine solution and dried (MgSO4). The EtOAc was evaporated to provide a residual oil. Chromatography (silica gel-EtOAc) gave product, 2.4 g.

Workup

  1. temperatureat reflux temperature for 16 h
  2. filtrationThe reaction mixture was filtered
  3. customsolvent was evaporated
  4. dissolutionThe residue was dissolved in EtOAc
  5. extractionthe solution was extracted with dilute HCl
  6. extractionThe basic mixture was extracted with EtOAc
  7. washThe organic solution was washed with brine solution
  8. dry with materialdried (MgSO4)
  9. customThe EtOAc was evaporated
  10. customto provide a residual oil
  11. customChromatography (silica gel-EtOAc) gave product, 2.4 g

Sources & evidence

ORD record
ord-aad34a3b993f46b0b26013357956bf64
Source dataset
uspto-grants-1994_03
Patent number
US05292766

Reaction notes

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