Methylamine → 3-(4-Fluorophenoxy)-N-methyl-1-azetidinecarboxamide

HRID 974603

Reaktionsgleichung

Reaktionsgleichung von HRID 974603
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]2)=[CH:4][CH:3]=1.[CH3:16][NH2:17]>O1CCCC1.C(Cl)Cl>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11]([NH:17][CH3:16])=[O:12])[CH2:8]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 6329MethylamineHCID 150533673-(4-Fluorophenoxy)-1-azetidinecarbonyl chloride

Produkt 1

HCID 150534373-(4-Fluorophenoxy)-N-methyl-1-azetidinecarboxamideAusbeute 129,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4.6 g (0.02 mole) of 3-(4-fluorophenoxy)-1-azetidinecarbonyl chloride in 15 ml of tetrahydrofuran was stirred while 6.2 g (0.08 mole) of 40% aqueous methylamine was added. The reaction mixture was exothermic and was allowed to cool to ambient temperature while stirring for 18 hr. The reaction mixture was diluted with 200 ml of ice water and the oil droplets which separated quickly crystallized. Filtration yielded 6.6 g of crude product. The solid was dissolved in 100 ml of methylene chloride, treated with 15 g of silica gel and stirred for 2 hr. The silica gel was removed by filtration and washed wit 200 ml of 50/50 ethyl acetatemethylene chloride. The combined filtrates were concentrated on a rotary evaporator, yielding 5.8 g of solid residue. The solid was recrystallized by dissolving in 22 ml of acetone and adding 88 ml of isopropyl ether. The volume was reduced to 40 ml by boiling under nitrogen atmosphere and upon cooling the product crystallized. Filtration yielded 2.95 (66.7%) of white crystals, m.p. 140°-142° C.

Aufarbeitung

  1. additionwas added
  2. customthe oil droplets which separated quickly
  3. customcrystallized
  4. filtrationFiltration
  5. customyielded 6.6 g of crude product
  6. additiontreated with 15 g of silica gel
  7. stirringstirred for 2 hr
  8. customThe silica gel was removed by filtration
  9. washwashed wit 200 ml of 50/50 ethyl acetatemethylene chloride
  10. concentrationThe combined filtrates were concentrated on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-f75f0d7ea04c43aaa84e1e4db2741c27
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05068231

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