Iodoethane → HCID 67375894, compound

HRID 522868Notes

Reaction equation

HRID 522868 reaction equation
[CH2:1]([N:8]1[CH2:20][CH2:19][C:11]2[NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:23](I)[CH3:24]>CN(C=O)C>[CH2:1]([N:8]1[CH2:20][CH2:19][C:11]2[N:12]([CH2:23][CH3:24])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 2754382-Benzyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indole

Product 1

HCID 67375894HCID 67375894, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-benzyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole and NaH (1.1 equiv.) in DMF (10 mL) was added at 0° C., ethyl iodide (1 mmol) and stirred at RT overnight. The reaction mixture was quenched with a sat. solution of NH4Cl and extracted with EtOAc. The combined organic extracts were dried over anydrous Na2SO4 and purified by flash chromatography to afford 2-benzyl-5-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (85%).

Workup

  1. additionwas added at 0° C.
  2. customThe reaction mixture was quenched with a sat. solution of NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over anydrous Na2SO4
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-b21adf4b106741d4bff918096ac50c7a
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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