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

HRID 1981363

Reaktionsgleichung

Reaktionsgleichung von HRID 1981363
[C:1]([OH:10])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N+:4]([O-:8])[CH:3]=1.CN(C1C=CC=CN=1)C.F[P-](F)(F)(F)(F)F.N1C2C=CC=C(O[P+](N(C)C)(N(C)C)N(C)C)C=2N=N1.[CH3:47][CH:48]1[CH2:53][CH2:52][CH2:51][N:50]([CH2:54][C:55]2[CH:56]=[C:57]([CH:63]=[CH:64][CH:65]=2)[O:58][CH2:59][CH2:60][CH2:61][NH2:62])[CH2:49]1>C(#N)C>[CH3:47][CH:48]1[CH2:53][CH2:52][CH2:51][N:50]([CH2:54][C:55]2[CH:56]=[C:57]([CH:63]=[CH:64][CH:65]=2)[O:58][CH2:59][CH2:60][CH2:61][NH:62][C:1]([C:2]2[CH:3]=[N+:4]([O-:8])[CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:49]1

Komponenten

6

Edukt 4

HCID 16976Oxiniacic AcidHCID 218852-DimethylaminopyridineHCID 140261883-{3-[(3-Methylpiperidin-1-yl)methyl]phenoxy}propan-1-amineHCID 178486078HCID 178486078, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a suspension of 2.8 g of nicotinic acid 1-oxide, 2.5 g of dimethylaminopyridine, 8.8 g of benzotriazolyloxy-tris-(dimethylamino)phosphonium hexafluorophosphate in 40 ml of acetonitrile, 5 g of 3-[3-(3-methylpiperidinomethyl)phenoxy]propylamine dissolved in 10 ml of acetonitrile are added at 20° C. under stirring. A rising of the temperature up to 30° C. is observed and a solution is obtained which is then stirred 2 hours at room temperature. The mixture is concentrated under reduced pressure, the residue is treated with 20 ml of concentrated sodium hydroxide and extracted 4 times with 40 ml of ethyl acetate. After evaporation of the organic extracts, the residue is purified by chromatography on silica as described in Example 7. Thus, the N-[3-[3-(3-methylpiperidinomethyl)phenoxy]propyl]-3-pyridinecarboxamide 1-oxide is obtained, identical to the product of Example 8.

Aufarbeitung

  1. additionare added at 20° C.
  2. customA rising of the temperature up to 30° C.
  3. customa solution is obtained which
  4. stirringis then stirred 2 hours at room temperature
  5. concentrationThe mixture is concentrated under reduced pressure
  6. additionthe residue is treated with 20 ml of concentrated sodium hydroxide
  7. extractionextracted 4 times with 40 ml of ethyl acetate
  8. customAfter evaporation of the organic extracts
  9. customthe residue is purified by chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-0569039e773c45058c59c1bbc81b622d
Quelldatensatz
uspto-grants-1985_04
Patentnummer
US04514408

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