Cyanoacetamide → 4-Cyano-2,3,5,6,7,8-hexahydro-1-methoxymethyl7-methyl-3-oxoisoquinoline

HRID 231225Notes

Reaction equation

HRID 231225 reaction equation
[CH3:1][O:2][CH2:3][C:4]([CH:6]1[CH2:11][CH:10]([CH3:12])[CH2:9][CH2:8][C:7]1=O)=O.[C:14]([CH2:16][C:17]([NH2:19])=[O:18])#[N:15].N1CCCCC1>C(O)C>[C:14]([C:16]1[C:17](=[O:18])[NH:19][C:4]([CH2:3][O:2][CH3:1])=[C:6]2[C:7]=1[CH2:8][CH2:9][CH:10]([CH3:12])[CH2:11]2)#[N:15]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 200349082-(2-Methoxyacetyl)-4-methylcyclohexan-1-one

Product 1

HCID 138498124-Cyano-2,3,5,6,7,8-hexahydro-1-methoxymethyl7-methyl-3-oxoisoquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Crude 2-methoxyacetyl-4-methylcyclohexanone, 3.7 g, 1.68 g of cyanoacetamide and 1 ml of piperidine were mixed with 50 ml of ethanol followed by heating to reflux for 4 hours. The precipitated crystals were taken out by filtration and purified to give 1.5 g of 4-cyano-2,3,5,6,7,8-hexahydro-1-methoxymethyl7-methyl-3-oxoisoquinoline.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 4 hours
  3. filtrationThe precipitated crystals were taken out by filtration
  4. custompurified

Sources & evidence

ORD record
ord-0a783edd073b4fdea159dddd620c1d6d
Source dataset
uspto-grants-1989_07
Patent number
US04845228

Reaction notes

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