4-Methylphenylhydrazine monohydrochloride → HCID 66612137, compound

HRID 1773282Notes

Reaction equation

HRID 1773282 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[CH:11]1([N:14]2[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]2)[CH2:13][CH2:12]1>S(=O)(=O)(O)O.O1CCOCC1>[CH:11]1([N:14]2[CH2:19][CH2:18][C:17]3[NH:9][C:6]4[CH:5]=[CH:4][C:3]([CH3:2])=[CH:8][C:7]=4[C:16]=3[CH2:15]2)[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 162276291-Cyclopropylpiperidin-4-one

Product 1

HCID 66612137HCID 66612137, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (4-methylphenyl)hydrazine hydrochloride (1.5 g, 0.00948 mol) and 1-cyclopropylpiperidin-4-one (1.3 g, 0.00948 mol) in 7% sulfuric acid in dioxane (20 mL) was heated at 80° C. for 2 h. The progress of reaction was monitored by TLC. After completion, the reaction mixture was cooled to RT and the dioxane layer was 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 affording crude material, which was purified by silica gel column chromatography (2% MeOH:DCM) to yield 2-cyclopropyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (1.4 g, 66% yield).

Workup

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

Sources & evidence

ORD record
ord-73369a54ba9d4132a8898fc9b4242219
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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