Cyanoacetamide → HCID 13632728, compound

HRID 621715Notes

Reaction equation

HRID 621715 reaction equation
[C:1]([CH:4]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][CH: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][CH:13]=[CH:12][CH:11]=1)[CH2:9]2)#[N:18]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 13632725HCID 13632725, compound

Product 1

HCID 13632728HCID 13632728, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.68 g of 2-acetyl-4-phenylcyclohexanone, 0.73 g of cyanoacetamide and a small amount of piperidine were mixed with 10 ml of ethanol and the obtained reaction mixture was heated under reflux for two hours. After cooling, the precipitated crystals were filtered and purified to give 1.5 g of 4-cyano-2,3,5,6,7,8-hexahydro-1-methyl- 3-oxo-7-phenylisoquinoline. m.p. >290° C. NMRδTMSDMSO-d6 : 1.90 (3H, m), 2.20 (3H, s), 2.80 (4H, m), 7.28 (5H, s) and 12.14 (1H, s).

Workup

  1. customthe obtained reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for two hours
  4. temperatureAfter cooling
  5. filtrationthe precipitated crystals were filtered
  6. custompurified

Sources & evidence

ORD record
ord-6d6a6fd4e52d41a19443c61103018aa5
Source dataset
uspto-grants-1989_04
Patent number
US04824952

Reaction notes

Loading…