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

HRID 621717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 621717
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 138498124-Cyano-2,3,5,6,7,8-hexahydro-1-methoxymethyl7-methyl-3-oxoisoquinolineAusbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

3.7 g of the crude 2-methoxyacetyl-4-methylcyclohexanone, 1.68 g of cyanoacetamide and 1 ml of piperidine were mixed with 50 ml of ethanol and the obtained reaction mixture was heated under reflux for four hours. The crystals thus formed were filtered and purified to give 1.5 g of 4-cyano-2,3,5,6,7,8-hexahydro-1-methoxymethyl-7-methyl-3-oxoisoquinoline. m.p.: 205°-208° C. NMRδTMSDMSO-d6 :1.01 (3H, d), 1.2-2.0 (4H, m), 2.5-2.6 (1H, m), 2.7-2.9 (2H, m), 3.28 (3H, s), 4.32 (2H, s) and 11.86 (1H, s).

Aufarbeitung

  1. customthe obtained reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for four hours
  4. customThe crystals thus formed
  5. filtrationwere filtered
  6. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-1b8999c98855439498d7b900291b7afd
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04824952

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