2-Chlorobenzoyl chloride → 2-Chloro-N-[6-(1-methyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide

HRID 30207

Reaktionsgleichung

Reaktionsgleichung von HRID 30207
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])[N:3]=1.[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>O1CCOCC1.CO>[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])[N:3]=1)=[O:21]

Komponenten

5

Edukt 2

HCID 691102-Chlorobenzoyl chlorideHCID 11401723(6-Aminopyridin-2-yl)(1-methylpiperidin-4-yl)methanone

Produkt 1

HCID 179803132-Chloro-N-[6-(1-methyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamideAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Mix 2-Amino-6-(1-methylpiperidin-4-ylcarbonyl)pyridine (0.223 g) and 2-chlorobenzoyl chloride (0.175 g) in 1,4-dioxane (10 mL) and heat at reflux for 1 hour. Dilute with methanol (10 mL) and load on a SCX column (10 g). Wash the column with methanol, elute the product with 2 M NH3 in methanol, evaporate and purify the product on a silica gel column (CH2Cl2 with 2 M NH3 in methanol) to obtain 0.305 g (84%) of the title compound: mass spectrum (electric spray) m/z=358 (M+1) and 360 (M+2+1); 1H NMR (CDCl3): 8.60 (br s, 1H), 8.54 (d, 1H), 7.90 (dd, 1H), 7.81 (d, 1H), 7.76 (dd, 1H), 7.45 (m, 3H), 3.63 (m, 1H), 2.90 (m, 2H), 2.29 (s, 3H), 2.07 (m 2H), 1.85 (m, 4H).

Aufarbeitung

  1. temperatureheat
  2. temperatureat reflux for 1 hour
  3. washWash the column with methanol
  4. washelute the product with 2 M NH3 in methanol
  5. customevaporate
  6. custompurify the product on a silica gel column (CH2Cl2 with 2 M NH3 in methanol)

Quellen und Nachweise

ORD-Eintrag
ord-da1977eecd694a5aad24d3161f0cae25
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423050B2

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