Methane → N-[[[1-[(6-Fluoro-2-naphthalenyl)methyl]-4-piperidinyl]amino]carbonyl]-4-pyridinecarboxamide

HRID 1382451Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1382451
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=3)[CH:10]=2)[CH2:4][CH2:3]1.[N:20]1[CH:25]=[CH:24][C:23]([C:26]([NH:28][C:29](N)=[O:30])=[O:27])=[CH:22][CH:21]=1.N1C=CC=CC=1.C>O.C(Cl)(Cl)Cl>[F:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([CH2:8][N:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:29]([NH:28][C:26]([C:23]3[CH:22]=[CH:21][N:20]=[CH:25][CH:24]=3)=[O:27])=[O:30])[CH2:3][CH2:4]1)[CH:18]=[CH:17]2

Komponenten

7

Edukt 4

HCID 297MethaneHCID 1049PyridineHCID 594347Piperidin-4-amine, 1-(6-fluoro-2-naphthylmethyl)-HCID 13851072Isonicotinoyl Urea

Produkt 1

HCID 13851073N-[[[1-[(6-Fluoro-2-naphthalenyl)methyl]-4-piperidinyl]amino]carbonyl]-4-pyridinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 4-amino-1-[(6-fluoro-2-naphthalenyl)methyl]piperidine (1.3 g, 5 mmol), 4-pyridoylurea (0.9 g, 5 mmol) and pyridine (6 ml) was stirred at reflux for 16 hours. The solution was diluted with water (8 ml) and the precipitated dark brown product collected by filtration to give 1.5 g. The crude product was dissolved in chloroform (25 ml), shaken with decolourising charcoal, filtered and evaporated. The residue was suspended in hot ethanol (20 ml) and succinic acid (0.44 g) added to give a clear solution which crystallised on standing. The product crystals were collected by filtration and washed with ethanol to give the succinate salt of the title compound. m.p. 187°-188° C.

Aufarbeitung

  1. temperatureat reflux for 16 hours
  2. filtrationthe precipitated dark brown product collected by filtration
  3. customto give 1.5 g
  4. filtrationfiltered
  5. customevaporated
  6. additionsuccinic acid (0.44 g) added
  7. customto give a clear solution which
  8. customcrystallised
  9. filtrationThe product crystals were collected by filtration
  10. washwashed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-3ed758330bdf4d23bcad696cbbf79575
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04806552

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