Hydrochloric Acid → HCID 21952753, compound

HRID 2215896Notes

Reaction equation

HRID 2215896 reaction equation
[ClH:1].C1(C)C=CC=C[C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14]N.Cl.O.[NH:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1.Cl>CCO>[ClH:1].[CH3:3][C:8]1[C:9]2[NH:14][C:22]3[CH2:21][CH2:20][NH:19][CH2:24][C:23]=3[C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723901PiperonylamineHCID 69291574HCID 69291574, compound

Product 1

HCID 21952753HCID 21952753, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

o-Tolylphenylhydrazine hydrogen chloride (25 g, 158.6 mmol) and 4-piperidone monohydrate hydrogen chloride (24.4 g, 158.6 mmol) were suspended in EtOH (310 mL). Concentrated aqueous HCl (26 g, 317 mmol) was then added. The mixture was refluxed for 3 h, and then the reaction was cooled to rt. The ppt was filtered and washed with cold EtOH. The white solid was air-dried for 18 h. 6-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride (36.6 g, 141.2 mmol, 89%) was isolated and a white powder. 1H NMR (CD3OD, 300 MHz) δ 7.22–7.25 (1H, m), 6.89–6.96 (2H, m), 4.40 (2H, m), 3.60 (2H, t, 6.2 Hz), 3.16 (2H, t, 6.2 Hz), 2.45 (3H, s) ppm.

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. filtrationThe ppt was filtered
  3. washwashed with cold EtOH
  4. customThe white solid was air-dried for 18 h

Sources & evidence

ORD record
ord-1eaafdaafeef4edbace1d8afe9475560
Source dataset
uspto-grants-2006_09
Patent number
US07109339B2

Reaction notes

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