Hydrochloric Acid → HCID 21952710, compound

HRID 735210Notes

Reaction equation

HRID 735210 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 minutes. Concentrated HCl (30 mL) was added and heated at reflux for 12 h. The reaction was cooled to room temperature, 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%). 1H NMR (CD3OD, 300 MHz) δ 7.24 (d, 1H, J=8.7 Hz), 7.08 (dd, 1H, J=0.7, 7.3 Hz), 6.93 (t, 1H, J=7.7 Hz), 3.29-3.27 (m, 2H), 3.17 (t, 2H, J=5.85 Hz), 2.85 (t, 2H, J=5.65 Hz), 2.44 (s, 3H) ppm.

Workup

  1. temperatureheated
  2. temperatureat reflux for 45 minutes
  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-f93455c184214811ac2a40f66d9f0f38
Source dataset
uspto-grants-2009_09
Patent number
US07592454B2

Reaction notes

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