Morpholine → 6-Morpholin-4-yl-4-phenoxy-nicotinic acid ethyl ester

HRID 2186790

Reaktionsgleichung

Reaktionsgleichung von HRID 2186790
[CH2:1]([O:3][C:4](=[O:19])[C:5]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][C:8](Cl)=[N:7][CH:6]=1)[CH3:2].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(N(CC)CC)C>O1CCCC1>[CH2:1]([O:3][C:4](=[O:19])[C:5]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][C:8]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[N:7][CH:6]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 54487232Ethyl 6-chloro-4-phenoxynicotinate

Produkt 1

HCID 538442216-Morpholin-4-yl-4-phenoxy-nicotinic acid ethyl esterAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 130 mg (0.468 mmol) 6-chloro-4-phenoxy-nicotinic acid ethyl ester, 0.040 ml (0.47 mmol) morpholine and 0.065 ml (0.47 mmol) triethylamine in 7 ml tetrahydrofuran was stirred at reflux for 40 h. After cooling to room temperature the reaction mixture was filtered, diluted with ethyl acetate and washed with water and saturated aqueous sodium chloride solution. The organic layer was dried with sodium sulfate and concentrated. Flash column chromatography afforded 66 mg (43%) of the title compound as a white solid.

Aufarbeitung

  1. temperatureat reflux for 40 h
  2. filtrationwas filtered
  3. additiondiluted with ethyl acetate
  4. washwashed with water and saturated aqueous sodium chloride solution
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4d8ed5848fb74aa381cbec85f77fba9b
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06407111B1

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