Iodoethane → HCID 12297101, compound

HRID 1656106Notes

Reaction equation

HRID 1656106 reaction equation
[CH2:1](I)[CH3:2].[CH2:4]1[C:9]2[NH:10][C:11]3[C:16]([C:8]=2[CH2:7][CH2:6][NH:5]1)=[CH:15][CH:14]=[CH:13][CH:12]=3.C(=O)([O-])O.[Na+]>C(#N)C>[CH2:6]([N:5]1[CH2:2][CH2:1][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH2:4]1)[CH3:7]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 107838Tetrahydro-beta-carbolineHCID 516892Sodium Bicarbonate

Product 1

HCID 12297101HCID 12297101, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl iodide (2.4 ml) was added to a solution of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (5.17 g) and sodium hydrogencarbonate (3.0 g) in 50 ml of acetonitrile and the solution was stirred at 70° C. over a bath for 3 hrs. After removal of the solvent by evaporation, water (60 ml) was added and the solution was extracted with chloroform. The extract was washed with brine and dried over magnesium sulfate. Purification of the crude product by silica gel column chromatography and crystallization from ethyl acetate of the eluates with methanol/chloroform (1/4) gave 1.5 g of 2-ethyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole.

Workup

  1. customAfter removal of the solvent
  2. customby evaporation, water (60 ml)
  3. additionwas added
  4. extractionthe solution was extracted with chloroform
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customPurification of the crude product
  8. customby silica gel column chromatography and crystallization from ethyl acetate of the eluates with methanol/chloroform (1/4)

Sources & evidence

ORD record
ord-16b152242987436f80e551b4f695d2ad
Source dataset
uspto-grants-1993_10
Patent number
US05252580

Reaction notes

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