1-Methyl-4-piperidone → HCID 66611743, compound

HRID 1773286Notes

Reaction equation

HRID 1773286 reaction equation
Cl.[CH:2]([C:5]1[CH:6]=[C:7]([NH:11]N)[CH:8]=[CH:9][CH:10]=1)([CH3:4])[CH3:3].[CH3:13][N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1>S(=O)(=O)(O)O.O1CCOCC1>[CH:2]([C:5]1[CH:10]=[CH:9][C:8]2[C:16]3[CH2:15][N:14]([CH3:13])[CH2:19][CH2:18][C:17]=3[NH:11][C:7]=2[CH:6]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 740491-Methyl-4-piperidoneHCID 44119127[3-(Propan-2-yl)phenyl]hydrazine--hydrogen chloride (1/1)

Product 1

HCID 66611743HCID 66611743, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (3-isopropylphenyl)hydrazine hydrochloride (5 g, 0.0267 mol) and 1-methyl-4-piperidone (3.3 mL, 0.0267 mol) in 7% sulfuric acid in dioxane (100 mL) was heated at 80° C. for 1 h. After completion, the reaction mixture was cooled to RT and the organic layer decanted. The residue was basified with 10% sodium hydroxide solution and extracted with EtOAc (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure affording crude material, which was purified by silica gel column chromatography (6% MeOH:DCM) to yield 7-isopropyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (1.1 g, 18% yield).

Workup

  1. customthe organic layer decanted
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customaffording crude material, which
  6. customwas purified by silica gel column chromatography (6% MeOH:DCM)

Sources & evidence

ORD record
ord-a553b379798545b1b96832f3e6efd723
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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