1-Sec-butyl-piperidin-4-one → 9-Sec.-butyl-1-methyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole

HRID 647936Notes

Reaction equation

HRID 647936 reaction equation
Cl.[NH:2]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[C:9]([CH3:12])[C:8]=2[CH:13]=1)N.[CH:14]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)([CH2:16][CH3:17])[CH3:15].C(O)(C)C.Cl>C(O)(C)C>[CH:14]([N:18]1[CH2:23][CH2:22][C:21]2[NH:2][C:4]3[C:13]([C:20]=2[CH2:19]1)=[C:8]1[C:9]([CH3:12])=[CH:10][S:11][C:7]1=[CH:6][CH:5]=3)([CH2:16][CH3:17])[CH3:15]

Participants

5

Reactant 3

HCID 131828071-Sec-butyl-piperidin-4-oneHCID 204843225-Hydrazino-3-methylbenzothiophene hydrochlorideHCID 21912024Isopropanol hydrochloride

Product 1

HCID 204842929-Sec.-butyl-1-methyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

11 g of 5-hydrazino-3-methylbenzothiophene hydrochloride and 8.5 g of 1-sec.-butyl-4-piperidone are boiled in 35 ml of isopropanol, and during this procedure isopropanol/HCl are added dropwise. The mixture is then evaporated, the residue is taken up in water and the mixture is rendered alkaline and extracted with methylene chloride. After washing and drying the organic phase, it is evaporated and the residue is recrystallised from cyclohexane. Melting point: 136°-137° C.

Workup

  1. customThe mixture is then evaporated
  2. extractionextracted with methylene chloride
  3. washAfter washing
  4. customdrying the organic phase, it
  5. customis evaporated
  6. customthe residue is recrystallised from cyclohexane

Sources & evidence

ORD record
ord-df7cf8c6b553416f8d8f5dedd3a353ab
Source dataset
uspto-grants-1983_10
Patent number
US04410536

Reaction notes

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