4-Methylphenylhydrazine monohydrochloride → 2-ethyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1401400Notes

Reaction equation

HRID 1401400 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.Cl.[CH2:12]([N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1)[CH3:13]>C(O)C>[CH2:12]([N:14]1[CH2:19][CH2:18][C:17]2[NH:8][C:5]3[CH:4]=[CH:3][C:2]([CH3:10])=[CH:7][C:6]=3[C:16]=2[CH2:15]1)[CH3:13]

Participants

4

Reactant 2

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 123199151-Ethylpiperidin-4-one--hydrogen chloride (1/1)

Product 1

HCID 594550662-ethyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleYield 91.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of p-tolylhydrazine hydrochloride (5.0 g, 31.5 mmol) in Ethanol (150 mL) was added 1-ethylpiperidin-4-one hydrochloride (4.0 g, 24.5 mmol) and heated at 80° C. for 16 h. After completion of the reaction (monitored by LCMS). The reaction mixture was concentrated to dryness and basified with aq. saturated NaHCO3, extracted with EtOAc, the organic layer was separated dried over sodium sulfate and concentrated under vacuum to obtain 4.8 g (Yield 71.0%) of 2-ethyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CDCl3, free base) δ (ppm) 7.7 (bs, 1H), 7.2-7.1 (m, 2H), 6.9 (d, 1H), 3.8 (s, 2H), 2.9 (s, 4H), 2.7 (q, 2H), 2.4 (s, 3H), 1.2 (t, 3H).

Workup

  1. customAfter completion of the reaction (monitored by LCMS)
  2. concentrationThe reaction mixture was concentrated to dryness
  3. extractionextracted with EtOAc
  4. customthe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-29c54278b6cf4357a7db2fe630950306
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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