Acetic Acid → HCID 58531372, Verbindung

HRID 1889688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1889688
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=2)=[CH:13][CH:12]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:18]=2)=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 673264-Fluorobenzylamine2×HCID 13942383-(4-Chlorophenyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 58531372HCID 58531372, VerbindungAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

To a homogeneous mixture of (4-fluorophenyl)methanamine (2.5 mL, 21.8 mmol) and 4′-chlorobiphenyl-3-carbaldehyde (Aldrich, 3.6 g, 16.8 mmol) in anhydrous dichloroethane (25 mL), under nitrogen atmosphere, was added acetic acid (1.2 mL, 21.0 mmol). The mixture was stirred at room temperature for 13.5 h before sodium triacetoxyborohydride (5.0 g, 23.5 mmol) was added. After 4 h, (4-fluorophenyl)methanamine (2.5 mL, 21.8 mmol) was added and the stirring continued. After an additional 5 h of stirring, the reaction was quenched with 1 N aq. NaOH solution (50 mL) then extracted twice with chloroform. The organic extracts were combined, washed with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography (Merck KGaA, 230-400 mesh particle size) eluting with 0-70% ethyl acetate in hexane, to afford the title compound (3.43 g, 59%) as a colorless oil. MS (ESI): 326.1 (M+H)+.

Aufarbeitung

  1. additionwas added
  2. customthe reaction was quenched with 1 N aq. NaOH solution (50 mL)
  3. extractionthen extracted twice with chloroform
  4. washwashed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel flash chromatography (Merck KGaA, 230-400 mesh particle size)
  9. washeluting with 0-70% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-0b7c915ef6c34d6ca8929ef09376ce51
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501992B2

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