HCID 67375894, compound → HCID 45094569, compound

HRID 522869Notes

Reaction equation

HRID 522869 reaction equation
C([N:8]1[CH2:22][CH2:21][C:11]2[N:12]([CH2:19][CH3:20])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9]1)C1C=CC=CC=1>CCO.[Pd]>[CH2:19]([N:12]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[C:10]2[CH2:9][NH:8][CH2:22][CH2:21][C:11]1=2)[CH3:20]

Participants

4

Reactant 1

HCID 67375894HCID 67375894, compound

Product 1

HCID 45094569HCID 45094569, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Benzyl-5-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (1 g) was dissolved in EtOH (10 mL), treated with 10% Pd/C (150 mg) and stirred under an atmosphere of hydrogen at RT. The reaction mixture was filtered through Celite® (diatomaceous earth) and concentrated. Purification by flash chromatography (10% MeOH/CH2Cl2) afforded 5-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (90%) as a viscous oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite® (diatomaceous earth)
  2. concentrationconcentrated
  3. customPurification by flash chromatography (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-1981e855c50945f498736135b6e5f4ce
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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