Cyanoacetamide → 2,3,5,6,7,8-Hexahydro-1-methyl-3-oxo-7-(4-pyridinyl)-4-isoquinolinecarbonitrile

HRID 621709Notes

Reaction equation

HRID 621709 reaction equation
[C:1]([CH:4]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH2:7][CH2:6][C:5]1=O)(=O)[CH3:2].[C:17]([CH2:19][C:20]([NH2:22])=[O:21])#[N:18].N1CCCCC1>C(O)C>[C:17]([C:19]1[C:20](=[O:21])[NH:22][C:1]([CH3:2])=[C:4]2[C:5]=1[CH2:6][CH2:7][CH:8]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)[CH2:9]2)#[N:18]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 137720552-Acetyl-4-(4-pyridyl)cyclohexanone

Product 1

HCID 136327302,3,5,6,7,8-Hexahydro-1-methyl-3-oxo-7-(4-pyridinyl)-4-isoquinolinecarbonitrileYield 34.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.65 g of 2-acetyl-4-(4-pyridyl)cyclohexanone and 0.64 g of cyanoacetamide were dissolved in ethanol and a small amount of piperidine was added thereto. The obtained reaction mixture was heated under reflux for seven hours. After the completion of the reaction, crystals thus precipitated out were filtered to give 0.7 g of 4-cyano-2,3,5,6,7,8-hexahydro-1-methyl-3-oxo-7-(4-pyridyl)isoquinoline.

Workup

  1. customThe obtained reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for seven hours
  4. customAfter the completion of the reaction, crystals
  5. customthus precipitated out
  6. filtrationwere filtered

Sources & evidence

ORD record
ord-40f4419a7eef47f2b0c9e89b5e60283b
Source dataset
uspto-grants-1989_04
Patent number
US04824952

Reaction notes

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