Triethylamine → N-[3-[3-(3-methylpiperidinomethyl)phenoxy]propyl]-3-pyridinecarboxamide 1-oxide

HRID 1981360

Reaktionsgleichung

Reaktionsgleichung von HRID 1981360
[C:1]([OH:10])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N+:4]([O-:8])[CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH3:26][CH:27]1[CH2:32][CH2:31][CH2:30][N:29]([CH2:33][C:34]2[CH:35]=[C:36]([CH:42]=[CH:43][CH:44]=2)[O:37][CH2:38][CH2:39][CH2:40][NH2:41])[CH2:28]1>C(Cl)Cl>[CH3:26][CH:27]1[CH2:32][CH2:31][CH2:30][N:29]([CH2:33][C:34]2[CH:35]=[C:36]([CH:42]=[CH:43][CH:44]=2)[O:37][CH2:38][CH2:39][CH2:40][NH:41][C:1]([C:2]2[CH:3]=[N+:4]([O-:8])[CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:28]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 16976Oxiniacic AcidHCID 62365Isobutyl chloroformateHCID 140261883-{3-[(3-Methylpiperidin-1-yl)methyl]phenoxy}propan-1-amine

Produkt 1

HCID 6917813N-[3-[3-(3-methylpiperidinomethyl)phenoxy]propyl]-3-pyridinecarboxamide 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of 0.03 mol of nicotinic acid 1-oxide in 40 ml of methylene chloride containing 10 ml of triethylamine, is added, at the temperature of from 0° to 5° C. and within about 10 minutes, 0.03 mol of isobutyl chloroformate dissolved in 15 ml of methylene chloride, then the mixture is stirred 30 minutes at the same temperature. To the same mixture and at the same temperature there is added 0.03 mol of 3-[3-(3-methylpiperidinomethyl)phenoxy]propylamine dissolved in 15 ml of methylene chloride, then, after a 2 hours stirring at room temperature, the reaction mixture is washed with 10 ml of water. The organic phase is filtered, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue is purified by chromatography on silica as described in Example 7 to yield the N-[3-[3-(3-methylpiperidinomethyl)phenoxy]propyl]-3-pyridinecarboxamide 1-oxide, identical to the product of Example 8.

Aufarbeitung

  1. stirringafter a 2 hours stirring at room temperature
  2. washthe reaction mixture is washed with 10 ml of water
  3. filtrationThe organic phase is filtered
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe residue is purified by chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-e107d24521254d3c8a70e851500540a7
Quelldatensatz
uspto-grants-1985_04
Patentnummer
US04514408

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