Hydrochloric Acid → 2,6-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1401412Notes

Reaction equation

HRID 1401412 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.Cl.[CH2:11](O)[CH3:12]>>[CH3:2][N:3]1[CH2:8][CH2:7][C:6]2[NH:3][C:4]3[C:11]([CH3:12])=[CH:8][CH:7]=[CH:6][C:5]=3[C:5]=2[CH2:4]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 122100571-Methylpiperidin-4-one hydrochloride

Product 1

HCID 5939582,6-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Conditions

Temperature
80 °C

Procedure

O-Tolyl hydrazine hydrochloride (3.0 g, 18.9 mmol) was dissolved in of ethanol (10 mL), 1-methylpiperidin-4-one hydrochloride (2.8 g, 18.9 mmol) and ethanolic HCl (10 mL) was added (pH acidic) and stirred at 80° C. for 5 h. Reaction was monitored by TLC. After completion of the reaction, reaction mixture was concentrated under vacuum. Residue was dissolved in aq NaHCO3 solution, extracted with EtOAc. Organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford 2.5 g of 2,6-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CDCl3, free base) δ (ppm) 7.65 (s, 1H), 7.01 (t, 1H), 6.9 (d, 1H), 3.61 (s, 2H), 2.89-2.80 (m, 4H), 2.58 (s, 3H), 2.41 (s, 3H).

Workup

  1. additionwas added (pH acidic)
  2. customReaction
  3. customAfter completion of the reaction, reaction mixture
  4. concentrationwas concentrated under vacuum
  5. dissolutionResidue was dissolved in aq NaHCO3 solution
  6. extractionextracted with EtOAc
  7. dry with materialOrganic layer was dried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5f5d05608007424395726ef5b559c823
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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