Cyanoacetamide → 4-Cyano-2,3,5,6,7,8-hexahydro-7-methoxy-1-methyl-3-oxoisoquinoline

HRID 980914Notes

Reaction equation

HRID 980914 reaction equation
[C:1]([CH:4]1[CH2:9][CH:8]([O:10][CH3:11])[CH2:7][CH2:6][C:5]1=O)(=O)[CH3:2].[C:13]([CH2:15][C:16]([NH2:18])=[O:17])#[N:14].N1CCCCC1>C(O)C>[C:13]([C:15]1[C:16](=[O:17])[NH:18][C:1]([CH3:2])=[C:4]2[C:5]=1[CH2:6][CH2:7][CH:8]([O:10][CH3:11])[CH2:9]2)#[N:14]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 136327242-Acetyl-4-methoxycyclohexanone

Product 1

HCID 136327264-Cyano-2,3,5,6,7,8-hexahydro-7-methoxy-1-methyl-3-oxoisoquinolineYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Acetyl-4-methoxycyclohexanone (1.02 g) and cyanoacetamide (0.462 g) were added to 5 ml of ethanol. After adding a small amount of piperidine, the mixture was heated under reflux for 2 hours. Deposited crystals were filtered out and recrystallized from methanol. There was obtained 0.42 g of 4-cyano-2,3,5,6,7,8-hexahydro-7-methoxy-1-methyl-3-oxoisoquinoline.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. filtrationDeposited crystals were filtered out
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-f3812168773e45588c957914eb8c6d0b
Source dataset
uspto-grants-1987_01
Patent number
US04639521

Reaction notes

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