1-Methylindole → HCID 22462569, compound

HRID 1936635Notes

Reaction equation

HRID 1936635 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.O.Cl.[CH3:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1>C(O)(=O)C.FC(F)(F)C(O)=O>[CH3:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:4]2[CH2:3][CH2:2][NH:1][CH2:6][CH:5]=2)=[CH:12]1

Participants

6

Reactant 3

HCID 117811-MethylindoleHCID 337214-PiperidoneHCID 21885828Hydrate;hydrochloride

Product 1

HCID 22462569HCID 22462569, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 4-piperidone. H2O.HCl (50 g, 0.32 mol) in 100 ml of acetic acid and 150 ml of trifluoroacetic acid was added dropwise a solution of 1-methylindole (11.5 ml, 0.09 mol) in 100 ml of acetic acid at room temperature. After stirring for 1h the reaction mixture was concentrated (in vacuum , temp. ca. 30° C.), water was added , the mixture was made basic with potassium carbonate and extracted with ethyl acetate. The organic layer was separated, dried and purified by silica gel column chromatography (dichloromethane/methanol/ammonium hydroxide =84/15/1) to give 9 g (47%) of the title compound.

Workup

  1. concentrationwas concentrated (in vacuum , temp. ca. 30° C.), water
  2. additionwas added
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. custompurified by silica gel column chromatography (dichloromethane/methanol/ammonium hydroxide =84/15/1)

Sources & evidence

ORD record
ord-fba3650eed98432f8a885c2928c2198a
Source dataset
uspto-grants-2002_05
Patent number
US06391896B1

Reaction notes

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