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

HRID 1981362

Reaktionsgleichung

Reaktionsgleichung von HRID 1981362
[C:1]([OH:10])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N+:4]([O-:8])[CH:3]=1.[CH:11]1(N=C=NC2CCCCC2)CCCCC1.C[CH:27]([N:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1)[C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][CH:38]=1)[O:31][CH2:32][CH2:33][CH2:34][NH2:35]>CN(C)C1C=CN=CC=1.C(#N)C>[CH3:11][CH:43]1[CH2:42][CH2:41][CH2:40][N:39]([CH2:27][C:28]2[CH:29]=[C:30]([CH:36]=[CH:37][CH:38]=2)[O:31][CH2:32][CH2:33][CH2:34][NH:35][C:1]([C:2]2[CH:3]=[N+:4]([O-:8])[CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:44]1

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 16976Oxiniacic AcidHCID 205671913-[3-(Methylpiperidinomethyl)phenoxy]propylamine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of 5 g of 4-dimethylaminopyridine in 80 ml of acetonitrile there is added 5.6 g of nicotinic acid 1-oxide. The mixture is stirred 10 minutes at room temperature and then added with 9.2 g of dicyclohexylcarbodiimide. After standing 5 minutes at room temperature, there are added 10 g of 3-[3-(methylpiperidinomethyl)phenoxy]propylamine dissolved in 20 ml of acetonitrile. A weakly exothermic reaction (from 20° to 25° C.) and a dissolution which within 5 minutes is almost completed, are observed. Then the mixture is stirred 4 hours at 40° C. and the dicyclohexylurea which forms is filtered and washed with acetonitrile. After evaporation to dryness under reduced pressure, 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; m.p. 108°-110° C.

Aufarbeitung

  1. waitAfter standing 5 minutes at room temperature
  2. customA weakly exothermic reaction (from 20° to 25° C.)
  3. dissolutiona dissolution which within 5 minutes
  4. stirringThen the mixture is stirred 4 hours at 40° C.
  5. filtrationthe dicyclohexylurea which forms is filtered
  6. washwashed with acetonitrile
  7. customAfter evaporation to dryness under reduced pressure
  8. customthe residue is purified by chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-058b48b2507348a19f6b9a22f71dfac1
Quelldatensatz
uspto-grants-1985_04
Patentnummer
US04514408

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