Acetone → N-Benzhydryl-3-(1,2,3-triazol-1-yl) azetidine

HRID 1742994

Reaktionsgleichung

Reaktionsgleichung von HRID 1742994
[CH:1]([N:14]1[CH2:17][CH:16]([N:18]=[N+:19]=[N-:20])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][C:22](C)=O>>[CH:1]([N:14]1[CH2:15][CH:16]([N:18]2[CH:22]=[CH:21][N:20]=[N:19]2)[CH2:17]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

3

Edukt 2

HCID 180AcetoneHCID 155126523-Azido-1-benzhydrylazetidine

Produkt 1

HCID 54270435N-Benzhydryl-3-(1,2,3-triazol-1-yl) azetidineAusbeute 76 %

Versuchsvorschrift

To a solution of 1.05 g (3.98 mmol) of N-benzhydryl-3-azidoazetidine in 50 ml of acetone cooled to -78° C. in a steel reaction vessel was bubbled 36 g of acetylene. The sealed reaction vessel after warming up to room temperature was heated at 80° C. for 17 hr. The solution was then cooled to room temperature, filtered and evaporated to yield the crude product which after chromatography over silica gel (2.5% methanol chloroform) yielded 0.88 g (76%) of the desired product as a solid, m.p. 167°-168° C. 1H NMR (CDCl3) δ: 7.88 (S, 1H), 7.73 (S, 1H), 7.55-7.07 (m, 10H), 5.35-5.1 (m, 1H), 4.53 (S, 1H), 3.76 (t, 2H), 3.5 (t, 2H).

Aufarbeitung

  1. customwas bubbled 36 g of acetylene
  2. customThe sealed reaction vessel
  3. temperaturewas heated at 80° C. for 17 hr
  4. temperatureThe solution was then cooled to room temperature
  5. filtrationfiltered
  6. customevaporated
  7. customto yield the crude product which after chromatography over silica gel (2.5% methanol chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-fc6907d3b15344a8881e6ae9fd5f3be0
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05342846

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