Tetrahydrofuran → HCID 19799597, Verbindung

HRID 1032122

Reaktionsgleichung

Reaktionsgleichung von HRID 1032122
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]1.[C:19](=[O:22])([O-:21])[O-].[K+].[K+].Br.Br.[CH2:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[CH2:28][CH3:29].[O:36]1CCCC1>O.CC(O)C>[C:5]([OH:36])(=[O:6])/[CH:14]=[CH:15]/[C:19]([OH:21])=[O:22].[CH2:27]([N:30]1[CH2:35][CH2:34][N:33]([C:11]([N:9]2[CH2:10][CH:7]([O:6][C:5]3[CH:14]=[CH:15][CH:16]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=3)[CH2:8]2)=[O:12])[CH2:32][CH2:31]1)[CH2:28][CH3:29]

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 3085288N-Propylpiperazinium dibromideHCID 197996061-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine

Produkt 1

HCID 19799597HCID 19799597, VerbindungAusbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 2.8 g (0.01 mole) of 3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride and 4.2 g (0.03 mole) of potassium carbonate in 25 ml of tetrahydrofuran was stirred for 10 min, then treated with 2.9 g (0.01 mole) of 1-propylpiperazine dihydrobromide in small portions. After 30 min, a few pieces of ice were added. After stirring for 17 hr, the reaction was diluted with 200 ml of water then extracted with methylene chloride (2×50 ml). The combined extracts were dried over magnesium sulfate and concentrated in vacuo, yielding 4.84 g of crude residue. The residue was converted to the fumarate salt in 2-propanol, concentrated to a solid in vacuo and recrystallized from acetone with a trace of ethanol to yield 2.9 g (59.5%) of fine white crystals; m.p. 117°-123° C.

Aufarbeitung

  1. waitAfter 30 min
  2. additiona few pieces of ice were added
  3. stirringAfter stirring for 17 hr
  4. extractionthen extracted with methylene chloride (2×50 ml)
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customyielding 4.84 g of crude residue
  8. concentrationconcentrated to a solid in vacuo
  9. customrecrystallized from acetone with a trace of ethanol

Quellen und Nachweise

ORD-Eintrag
ord-696ec00132224894a5fccc3f690cc770
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04956359

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