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

HRID 980909Notes

Reaction equation

HRID 980909 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

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

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 7 hours
  3. filtrationwere filtered out

Sources & evidence

ORD record
ord-c14929ee32b140db81e84a83b3e6b75d
Source dataset
uspto-grants-1987_01
Patent number
US04639521

Reaction notes

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