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

HRID 231220Notes

Reaction equation

HRID 231220 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

With 5 ml of ethanol were mixed 1.02 g of 2-acetyl-4methoxycyclohexanone and 0.462 g of cyanoacetamide and, a small quantity of piperidine was added to the mixture followed by heating to reflux for 2 hours. The precipitated crystals were taken out by filtration and recrystallized from methanol to give 0.42 g of 4-cyano-2,3,5,6,7,8-hexahydro-7-methoxy-1-methyl-3-oxoisoquinoline.

Workup

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

Sources & evidence

ORD record
ord-9c55db9b105d49a7bd4b07e7eee2d59c
Source dataset
uspto-grants-1989_07
Patent number
US04845228

Reaction notes

Loading…