Water → 4-chloro-2-(N-(2-morpholin-4-ylethyl)carbamoyl)pyridine

HRID 598439

Reaktionsgleichung

Reaktionsgleichung von HRID 598439
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([O:11]C)=O)[CH:4]=1.[NH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.O>C1COCC1>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9](=[O:11])[NH:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:4]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4082852-MorpholinoethylamineHCID 16655470Methyl 4-chloropyridine-2-carboxylate--hydrogen chloride (1/1)

Produkt 1

HCID 236145794-chloro-2-(N-(2-morpholin-4-ylethyl)carbamoyl)pyridineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-chloropyridine-2-carboxylate HCl salt Method A2, Step 2; 1.01 g, 4.86 mmol) in THF (20 mL) was added 4-(2-aminoethyl)morpholine (2.55 mL, 19.4 mmol) dropwise and the resulting solution was heated at the reflux temp. for 20 h, cooled to room temp., and treated with water (50 mL). The resulting mixture was extracted with EtOAc (50 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford 4-chloro-2-(N-(2-morpholin-4-ylethyl) carbamoyl)pyridine as a yellow oil (1.25 g, 95%): TLC (10% MeOH/90% EtOAc) Rf 0.50.

Aufarbeitung

  1. temperaturethe resulting solution was heated at the reflux temp
  2. temperaturecooled to room temp.
  3. extractionThe resulting mixture was extracted with EtOAc (50 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c47df103d12346a6846e02ad2c285b48
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897623B2

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