4-Piperidone → 7.8,9,10-Tetrahydrothieno[3.2-e]pyrido[4,3-b]indole

HRID 647924Notes

Reaction equation

HRID 647924 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.[NH:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1>C(O)(C)C>[CH:9]1[C:8]2=[C:12]3[C:4](=[CH:5][CH:6]=[C:7]2[S:11][CH:10]=1)[NH:2][C:16]1[CH2:17][CH2:18][NH:13][CH2:14][C:15]3=1

Participants

4

Reactant 2

HCID 337214-PiperidoneHCID 20484314(1-Benzothiophen-5-yl)hydrazinehydrochloride

Product 1

HCID 212492377.8,9,10-Tetrahydrothieno[3.2-e]pyrido[4,3-b]indole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

15 g of 5-hydrazinobenzothiophene hydrochloride and 15 g of 4-piperidone are boiled in 450 ml of isopropanol under a reflux condenser for 2 hours. After cooling the mixture, the precipitate which has separated out is filtered off and suspended in 2 N NaOH. A layer of methylene chloride is introduced under the suspension and the mixture is stirred; the layers are then separated and the organic phase is washed, dried and evaporated. After recrystallisation of the residue from isopropanol, 7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole of melting point 190° is obtained.

Workup

  1. temperatureAfter cooling the mixture
  2. customthe precipitate which has separated out
  3. filtrationis filtered off
  4. additionA layer of methylene chloride is introduced under the suspension
  5. customthe layers are then separated
  6. washthe organic phase is washed
  7. customdried
  8. customevaporated
  9. customAfter recrystallisation of the residue from isopropanol, 7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole of melting point 190°
  10. customis obtained

Sources & evidence

ORD record
ord-aa943656867f46beaa127ff12ce24459
Source dataset
uspto-grants-1983_10
Patent number
US04410536

Reaction notes

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