Cyanoacetamide → 3-Hydroxy-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile

HRID 980917Notes

Reaction equation

HRID 980917 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=O)(=O)[CH3:2].[C:11]([CH2:13][C:14]([NH2:16])=[O:15])#[N:12].N1CCCCC1>C(O)C>[C:11]([C:13]1[C:14](=[O:15])[NH:16][C:1]([CH3:2])=[C:4]2[C:9]=1[CH2:8][CH2:7][CH2:6][CH2:5]2)#[N:12]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 134002-Acetylcyclohexanone

Product 1

HCID 13896753-Hydroxy-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Acetylcyclohexanone (5 g) and cyanoacetamide (3 g) were added to 25 ml of ethanol and a small amount of piperidine was also added. The mixture was heated under reflux for 2 hours. After cooling, deposited crystals were filtered out and washed with ethanol. There was obtained 4.5 g of 4-cyano-2,3,5,6,7,8-hexahydro-1-methyl-3-oxoisoquinoline.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. filtrationdeposited crystals were filtered out
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-3b01498f39554ec9a6a3f9b04dfcebb3
Source dataset
uspto-grants-1987_01
Patent number
US04639521

Reaction notes

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