Piperonylamine → 1-Phenyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole

HRID 647942Notes

Reaction equation

HRID 647942 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.O.Cl.[NH:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1>C(O)(C)C>[C:12]1([C:9]2[C:8]3=[C:18]4[C:4](=[CH:5][CH:6]=[C:7]3[S:11][CH:10]=2)[NH:2][C:24]2[CH2:25][CH2:26][NH:21][CH2:22][C:23]4=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 2723901PiperonylamineHCID 204842955-Hydrazino-3-phenylbenzothiophene hydrochloride

Product 1

HCID 204843051-Phenyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

28 g of 5-hydrazino-3-phenylbenzothiophene hydrochloride are dissolved in 300 ml of isopropanol and the solution is combined with 20 g of 4-piperidone hydrochloride monohydrate under an inert gas. After boiling the mixture for 3 hours, the solvent is evaporated off, the residue is taken up in isopropanol and the product is precipitated with the addition of isopropyl ether. The precipitate is filtered off and taken up in water; a layer of methylene chloride is introduced under the solution and the mixture is shaken with NaOH solution. The organic phase is separated off and worked up. Melting point: 228° C. (decomposition)

Workup

  1. customfor 3 hours
  2. customthe solvent is evaporated off
  3. customthe product is precipitated with the addition of isopropyl ether
  4. filtrationThe precipitate is filtered off
  5. additiona layer of methylene chloride is introduced under the solution
  6. customThe organic phase is separated off

Sources & evidence

ORD record
ord-241ef8d045ff4f6b9001c250146e9c54
Source dataset
uspto-grants-1983_10
Patent number
US04410536

Reaction notes

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