Cyanoacetamide → HCID 13632727, compound

HRID 621713Notes

Reaction equation

HRID 621713 reaction equation
[C:1]([CH:4]1[CH2:9][CH:8]([CH3:10])[CH2:7][CH2:6][C:5]1=O)(=O)[CH3:2].[C:12]([CH2:14][C:15]([NH2:17])=[O:16])#[N:13].N1CCCCC1>C(O)C>[C:12]([C:14]1[C:15](=[O:16])[NH:17][C:1]([CH3:2])=[C:4]2[C:5]=1[CH2:6][CH2:7][CH:8]([CH3:10])[CH2:9]2)#[N:13]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 14911578HCID 14911578, compound2×

Product 1

HCID 13632727HCID 13632727, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the total amount of the crude 2-acetyl-4methylcyclohexanone prepared in (1), 35 ml of ethanol, 3.36 g of cyanoacetamide and a small amount of piperidine were added and the obtained reaction mixture was heated under reflux for four hours. The crystals thus precipitated were filtered and recrystallized from a mixture of methanol and water to give 4.22 g of 4-cyano-1,7-dimethyl-2,3,5,6,7,8hexahydro-3-oxoisoquinoline. m.p. >290° C. NMRδTMSCF3COOH : 1.23 (3H, d), 2.60 (3H, s) and 1.8-3.3 (7H,m).

Workup

  1. customthe obtained reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for four hours
  4. customThe crystals thus precipitated
  5. filtrationwere filtered
  6. customrecrystallized from a mixture of methanol and water

Sources & evidence

ORD record
ord-66ec3a147add45cbb1ebdd4deca14986
Source dataset
uspto-grants-1989_04
Patent number
US04824952

Reaction notes

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