Sodium Azide → HCID 178442109, Verbindung

HRID 483013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 483013
[N-:1]=[N+:2]=[N-:3].[Na+].C([O:8][C:9]1[CH:18]=[C:17]([O:19][CH:20]([CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:21])[CH:16]=[C:15]2[C:10]=1[CH:11]([CH2:35][CH2:36][C:37]#[N:38])[CH2:12][CH:13]1[CH2:34][CH2:33][CH2:32][CH2:31][N:14]12)(=O)C.Cl.CN1CCCCC1>CN1CCCCC1.C(O)C>[OH:8][C:9]1[CH:18]=[C:17]([O:19][CH:20]([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH3:21])[CH:16]=[C:15]2[C:10]=1[CH:11]([CH2:35][CH2:36][C:37]1[NH:38][N:3]=[N:2][N:1]=1)[CH2:12][CH:13]1[CH2:34][CH2:33][CH2:32][CH2:31][N:14]12

Komponenten

6

Edukt 3

HCID 33557Sodium AzideHCID 205378Piperidine, 1-methyl-, hydrochloride (1:1)2×HCID 20443048HCID 20443048, Verbindung

Produkt 1

HCID 178442109HCID 178442109, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 12291N-MethylpiperidineKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Finely ground sodium azide (325 mg., 5 mmole) is added to a solution of 7 -acetoxy-6-(2-cyanoethyl)-9-(5-phenyl-2-pentyloxy)-2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinoline (506 mg., 1 mmole) in 5 ml. of 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 mmole of N-methylpiperidine hydrochloride is added, refluxing continued for another hour and allowed to stand overnight at room temperature. The mixture is partitioned between chloroform and aqueous sodium carbonate solution. The aqueous layer is adjusted to pH 5, extracted again with chloroform and the combined organic layers washed with water and the chloroform is dried (MgSO4). Evaporation of solvent under reduced pressure affords the title compound.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureat reflux for one hour
  3. temperaturerefluxing
  4. waitcontinued for another hour
  5. customThe mixture is partitioned between chloroform and aqueous sodium carbonate solution
  6. extractionextracted again with chloroform
  7. washthe combined organic layers washed with water
  8. dry with materialthe chloroform is dried (MgSO4)
  9. customEvaporation of solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-381b4980f3434182ae2bc482d8ca86dd
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04576964

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