Dimethyl Sulfoxide → 6-[p-(4-Piperidinopiperidino)phenyl]-1,2-dihydro-2-oxonicotinonitrile

HRID 972683

Reaktionsgleichung

Reaktionsgleichung von HRID 972683
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:16])[C:11](=[CH:14][CH:15]=2)[C:12]#[N:13])=[CH:4][CH:3]=1.[N:17]1([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.CS(C)=O>C(O)C>[N:17]1([CH:23]2[CH2:28][CH2:27][N:26]([C:2]3[CH:7]=[CH:6][C:5]([C:8]4[NH:9][C:10](=[O:16])[C:11](=[CH:14][CH:15]=4)[C:12]#[N:13])=[CH:4][CH:3]=3)[CH2:25][CH2:24]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 786071,4'-BipiperidineHCID 27652036-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Produkt 1

HCID 214045226-[p-(4-Piperidinopiperidino)phenyl]-1,2-dihydro-2-oxonicotinonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 10.7 g. of 6-(p-fluorophenyl)-1,2-dihydro-2-oxonicotinonitrile [J. Med. Chem. 14, 342 (1971)] and 16.8 g. of 4-piperidinopiperidine in 140 ml. of dimethyl sulfoxide is stirred and heated at 95°-100° for 50 hours. The mixture is cooled and diluted with 450 ml. of 95% ethanol. The resulting precipitate of 6-[p-(4-piperidinopiperidino)phenyl]-1,2-dihydro-2-oxonicotinonitrile is collected by filtration, washed with 95% ethanol and dried; m.p. 288°-293° (dec.).

Aufarbeitung

  1. additionA mixture of 10.7 g
  2. temperatureheated at 95°-100° for 50 hours
  3. temperatureThe mixture is cooled
  4. additiondiluted with 450 ml
  5. filtrationThe resulting precipitate of 6-[p-(4-piperidinopiperidino)phenyl]-1,2-dihydro-2-oxonicotinonitrile is collected by filtration
  6. washwashed with 95% ethanol
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0a73f4e52c7e4167862210c979e4bd9a
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04053470

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