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

HRID 621711Notes

Reaction equation

HRID 621711 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

1.02 g of 2-acetyl-4-methoxycyclohexanone and 0.462 g of cyanoacetamide were mixed with 5 ml of ethanol and a small amount of piperidine was added thereto. The obtained reaction mixture was heated under reflux for two hours. The crystals thus precipitated were filtered 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. m.p. 257°-259° C. NMRTMSCF3COOH : 2.25 (2H, m), 2.57 (3H, s), 2.97 (2H, m), 3.20 (2H, m), 3.66 (3H, s) and 4.16 (1H, m).

Workup

  1. customThe obtained reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for two hours
  4. customThe crystals thus precipitated
  5. filtrationwere filtered
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-d2208649ebda4198a0a180cb62ab453e
Source dataset
uspto-grants-1989_04
Patent number
US04824952

Reaction notes

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