1H-Pyrrolo(2,3-b)pyridine → 4-{1H-pyrrolo[2,3-b]pyridin-3-yl}-1,2,3,6-tetrahydropyridine

HRID 324959Notes

Reaction equation

HRID 324959 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[NH:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1.[OH-].[K+]>CO>[NH:10]1[CH2:11][CH:12]=[C:13]([C:3]2[C:4]3[C:9](=[N:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14797Potassium HydroxideHCID 337214-Piperidone

Product 1

HCID 148220634-{1H-pyrrolo[2,3-b]pyridin-3-yl}-1,2,3,6-tetrahydropyridineYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Azaindole (10 g, 85 mmol), 4piperidone (34 g,0.22 mol) and potassium hydroxide (16.83 g, 0.3 mol) were heated to reflux in 150 ml methanol overnight. The reaction was cooled, filtered and concentrated to give an orange slurry. The slurry was then extracted with methylene chloride and washed with water. The organic layer was dried over anhydrous magnesium, filtered and concentrated to afford 14.2 g (84%) of product as a solid: mp 195-199° C.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customto give an orange slurry
  5. extractionThe slurry was then extracted with methylene chloride
  6. washwashed with water
  7. dry with materialThe organic layer was dried over anhydrous magnesium
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b4e1d97b78a2464ba382a91dd654c282
Source dataset
uspto-grants-2001_04
Patent number
US06221863B1

Reaction notes

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