Hydrochloric Acid → HCID 21952710, compound

HRID 2215890Notes

Reaction equation

HRID 2215890 reaction equation
[ClH:1].[CH3:2][S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10]N.Cl.O.[NH:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.Cl>C(O)C>[ClH:1].[CH3:2][S:3][C:4]1[C:5]2[NH:10][C:17]3[CH2:18][CH2:19][NH:14][CH2:15][C:16]=3[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723901PiperonylamineHCID 21952754[2-(Methylsulfanyl)phenyl]hydrazine hydrochloride

Product 1

HCID 21952710HCID 21952710, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-Methylsulfanyl-phenyl)hydrazine hydrochloride (27 g, 141.9 mmol) and 4-piperidone monohydrate hydrochloride (21.8 g, 141.9 mmol) were dissolved in ethanol (350 mL) and heated at reflux for 45 min. Conc. HCl (30 mL) was added and heated at reflux for 12 h. The reaction was cooled to rt, filtered, washed with cold isopropyl alcohol (50 mL), and dried to give an off white solid, 6-methylsulfanyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride (33 g, 92%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 45 min
  3. temperatureheated
  4. temperatureat reflux for 12 h
  5. filtrationfiltered
  6. washwashed with cold isopropyl alcohol (50 mL)
  7. customdried

Sources & evidence

ORD record
ord-e63c6e3d56e54d62939c8a2ce2e95404
Source dataset
uspto-grants-2006_09
Patent number
US07109339B2

Reaction notes

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