Ethanol → HCID 178442730, Verbindung

HRID 1608434Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1608434
[N-:1]=[N+:2]=[N-:3].[Na+].C([O:8][C:9]1[C:14]2[CH:15]([C:21]#[N:22])[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:13]=2[CH:12]=[C:11]([C:23]([CH3:31])([CH3:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:10]=1)(=O)C.C(O)C.Cl.CN1CCCCC1>CN1CCCCC1>[OH:8][C:9]1[C:14]2[CH:15]([C:21]3[NH:22][N:3]=[N:2][N:1]=3)[CH2:16][C:17]([CH3:19])([CH3:20])[O:18][C:13]=2[CH:12]=[C:11]([C:23]([CH3:30])([CH3:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:10]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 33557Sodium AzideHCID 205378Piperidine, 1-methyl-, hydrochloride (1:1)HCID 19848841HCID 19848841, Verbindung

Produkt 1

HCID 178442730HCID 178442730, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12291N-MethylpiperidineKatalysator

Versuchsvorschrift

Finely ground sodium azide (325 mg, 5 mmole) is added to a solution of 5-acetoxy-4-cyano-2,2-dimethyl-7-(1,1-dimethylheptyl)-3,4-dihydro-2H-benzopyran (1.855 g, 5 mmole) in 10 ml ethanol-free chloroform containing 271 mg (2 mmole) N-methylpiperidine hydrochloride and 5 drops of N-methylpiperidine. The mixture is heated at reflux for one hour, another 2 mmoles of N-methylpiperidine hydrochloride is added, refluxing is continued for one hour and the mixture is allowed to stand overnight at room temperature. The mixture is partitioned between chloroform and aqueous sodium carbonate solution, the aqueous phase is adjusted to pH 5 and extracted again with chloroform. The combined organic layers are washed with water, dried (MgSO4) and the solvent evaporated in vacuo to afford the title compound.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureat reflux for one hour
  3. temperaturerefluxing
  4. waitto stand overnight at room temperature
  5. customThe mixture is partitioned between chloroform and aqueous sodium carbonate solution
  6. extractionextracted again with chloroform
  7. washThe combined organic layers are washed with water
  8. dry with materialdried (MgSO4)
  9. customthe solvent evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-35d25537c969442fac4b1659cc0f247f
Quelldatensatz
uspto-grants-1989_09
Patentnummer
US04870084

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