Triethylamine → 1-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone

HRID 710487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710487
[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][NH:3][CH2:2]1.CCN(CC)CC.[O:19](C(C(F)(F)F)=O)[C:20]([C:22]([F:25])([F:24])[F:23])=O>C(Cl)Cl>[F:23][C:22]([F:25])([F:24])[C:20]([N:3]1[CH2:2][CH2:1][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4]1)=[O:19]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 14002432,3,4,5-Tetrahydro-1H-benzo(d)azepine

Produkt 1

HCID 218871391-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanoneAusbeute 101,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.25 g, 1.7 mmol) in anhydrous CH2Cl2 (5 ml), Et3N (0.28 ml, 2 mmol) was added at 0° C. and under N2, followed by (CF3CO)2O (0.29 ml, 2 mmol) and the resulting mixture was stirred for 1 h, than washed with aqueous NaHCO3 and H2O. The organic layer was dried over MgSO4, filtered and the filtrate was evaporated to dryness to give the title product (0.418 g, 100%), as pale oil. 1H-NMR (CDCl3) 3.6-3.97 (m, 8H); 7.11-7.19 (m, 4H).

Aufarbeitung

  1. washthan washed with aqueous NaHCO3 and H2O
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-7cd3c541c1d44bb886532d7f0a090c41
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181182B2

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