Hydrochloric Acid → 9-Ethyl-1-phenyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole

HRID 647951Notes

Reaction equation

HRID 647951 reaction equation
Cl.[NH:2]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]=2[CH:18]=1)N.[CH2:19]([N:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1)[CH3:20].Cl>C(O)(C)C>[CH2:19]([N:21]1[CH2:26][CH2:25][C:24]2[NH:2][C:4]3[C:18]([C:23]=2[CH2:22]1)=[C:8]1[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][S:11][C:7]1=[CH:6][CH:5]=3)[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 771591-Ethylpiperidin-4-oneHCID 204842955-Hydrazino-3-phenylbenzothiophene hydrochloride

Product 1

HCID 204842879-Ethyl-1-phenyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

13.8 g of 5-hydrazino-3-phenylbenzothiophene hydrochloride and 6.7 g of 1-ethyl-4-piperidone are stirred in 60 ml of absolute isopropanol for 1 hour, the same amount of isopropanol containing hydrogen chloride is then added and the mixture is boiled under reflux for 4 hours. After evaporating off the solvent, the residue is treated with N NaOH and the base is extracted with methylene chloride. The substance, recrystallised from toluene, melts at 233° C., with decomposition.

Workup

  1. additionis then added
  2. temperatureunder reflux for 4 hours
  3. customAfter evaporating off the solvent
  4. additionthe residue is treated with N NaOH
  5. extractionthe base is extracted with methylene chloride
  6. customThe substance, recrystallised from toluene, melts at 233° C., with decomposition.

Sources & evidence

ORD record
ord-626185cade644c77afa5eb62efb16d99
Source dataset
uspto-grants-1983_10
Patent number
US04410536

Reaction notes

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