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

HRID 647925Notes

Reaction equation

HRID 647925 reaction equation
Cl.[NH:2]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)N.Cl.[CH3:14][N:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.Cl>C(O)(C)C>[CH3:14][N:15]1[CH2:20][CH2:19][C:18]2[NH:2][C:4]3[C:12]([C:17]=2[CH2:16]1)=[C:8]1[CH:9]=[CH:10][S:11][C:7]1=[CH:6][CH:5]=3

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 122100571-Methylpiperidin-4-one hydrochlorideHCID 20484314(1-Benzothiophen-5-yl)hydrazinehydrochloride

Product 1

HCID 204843279-Methyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

4 g of 5-hydrazinobenzothiophene hydrochloride, suspended in 100 ml of isopropanol, are combined with 2.8 ml of 1-methyl-4-piperidone hydrochloride under N2. The solution is brought to the boil and 10 ml of isopropanol saturated with HCl re added whilst the solution is hot. After boiling the mixture of 1/2 hour, the solvent is distilled off, the residue is treated with ammonia and the precipitate is filtered off and recrystallised from methanol. 9-Methyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole of melting point 189° C. is obtained.

Workup

  1. additionre added whilst the solution
  2. additionthe mixture of 1/2 hour
  3. distillationthe solvent is distilled off
  4. additionthe residue is treated with ammonia
  5. filtrationthe precipitate is filtered off
  6. customrecrystallised from methanol

Sources & evidence

ORD record
ord-15da22b4292a49c7b25f89e450fca20b
Source dataset
uspto-grants-1983_10
Patent number
US04410536

Reaction notes

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