4-Methylmorpholine → N-[2-(3-methoxy-phenyl)-ethyl]-4-pentafluoroethyl-benzamide

HRID 2244343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244343
[F:1][C:2]([F:16])([C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)[C:3]([F:6])([F:5])[F:4].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:25][CH2:26][NH2:27])[CH:22]=[CH:23][CH:24]=1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:25][CH2:26][NH:27][C:11](=[O:13])[C:10]2[CH:9]=[CH:8][C:7]([C:2]([F:1])([F:16])[C:3]([F:4])([F:5])[F:6])=[CH:15][CH:14]=2)[CH:22]=[CH:23][CH:24]=1

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 748663-MethoxyphenethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 230678834-(1,1,2,2,2-Pentafluoroethyl)benzoic acid

Produkt 1

HCID 86615231N-[2-(3-methoxy-phenyl)-ethyl]-4-pentafluoroethyl-benzamideAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-pentafluoroethyl-benzoic acid (500 mg, 2.08 mmol), 2-(3-methoxyphenyl)-ethylamine (361 mg, 2.29 mmol), 4-methylmorpholine (632 mg, 6.24 mmol), and HBTU (1.19 g, 3.12 mmol) in DMF (38 mL) was stirred at RT for 16 h, then the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded the title compound (746 mg, 96%). Light yellow solid, MS (ISP) 374.2 (M+H)+.

Aufarbeitung

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2a2903d4d33c421da9f5fda3104f999c
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678818B2

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