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

HRID 1400324Notes

Reaction equation

HRID 1400324 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-d2f3646604bd4a5f9e2e646b52ac5843
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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