Phenylhydrazine hydrochloride → 2-Ethyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indole

HRID 1400322Notes

Reaction equation

HRID 1400322 reaction equation
Cl.[C:2]1([NH:8]N)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:11]([N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1)[CH3:12]>C(O)C>[CH2:11]([N:13]1[CH2:18][CH2:17][C:16]2[NH:8][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:15]=2[CH2:14]1)[CH3:12]

Participants

4

Reactant 2

HCID 60962Phenylhydrazine hydrochlorideHCID 123199151-Ethylpiperidin-4-one--hydrogen chloride (1/1)

Product 1

HCID 5888242-Ethyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of phenylhydrazine hydrochloride (1 equiv) in ethanol was added 1-ethylpiperidin-4-one hydrochloride (1 equiv) and heated at 80° C. for 16 h. After completion of the reaction (monitored by LCMS). The reaction mixture was concentrated under vacuum and basified with aq. saturated NaHCO3, extracted with EtOAc, the organic layer was separated dried over sodium sulfate and concentrated under reduced pressure to obtain 2-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CDCl3, free base) δ (ppm) 7.8 (bs, 1H), 7.4 (d, 1H), 7.2-7.0 (m, 3H), 3.7 (s, 2H), 2.9 (s, 4H), 2.7-2.6 (q, 2H), 1.2 (t, 3H).

Workup

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

Sources & evidence

ORD record
ord-1904ff8918044c198b23b1a81f898bd5
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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