Dimethylformamide → HCID 12668986, compound

HRID 1656105Notes

Reaction equation

HRID 1656105 reaction equation
C1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4]CN1.[H-].[Na+].[CH3:16]I.[CH3:18][N:19]([CH:21]=O)[CH3:20]>>[CH3:18][N:19]1[CH2:21][CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:12]([CH3:16])[C:13]=2[CH2:20]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 107838Tetrahydro-beta-carboline

Product 1

HCID 12668986HCID 12668986, compound

Procedure

1,2,3,4-Tetrahydro-β-carboline (2.35 g) and NaH (60% nujol, 1.20 g) were added to anhydrous DMF and stirred at room temperature for 30 minutes. To the ice-cooled reaction solution was added methyl iodide (1.7 ml) and the reaction solution was stirred overnight. After removal of DMF by evaporation, the residue was mixed with water and extracted with chloroform. The extract was washed with water and dried over sodium sulfate. The crude product was purified by column chromatography on silica gel. Eluates with 5% methanol/chloroform afforded 1.6 g of 2,9-dimethyl-1,2,3,4-tetrahydro-β-carboline.

Workup

  1. customreaction solution
  2. stirringthe reaction solution was stirred overnight
  3. customAfter removal of DMF
  4. customby evaporation
  5. additionthe residue was mixed with water
  6. extractionextracted with chloroform
  7. washThe extract was washed with water
  8. dry with materialdried over sodium sulfate
  9. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-77ea3858e76e47c283e3780234b61db6
Source dataset
uspto-grants-1993_10
Patent number
US05252580

Reaction notes

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