Methanol → HCID 22643448, Verbindung

HRID 929722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929722
CO.[CH3:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.[F:12][C:13]([F:24])([F:23])[C:14]([N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)=[O:15].[BH3-]C#N.[Na+]>CO.C(O)(=O)C.C(O)(=O)C>[CH3:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH:9][CH:19]2[CH2:20][CH2:21][N:16]([C:14](=[O:15])[C:13]([F:12])([F:23])[F:24])[CH2:17][CH2:18]2)=[CH:6][CH:5]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 660354-MethylbenzylamineHCID 5003444Sodium cyanoborohydrideHCID 150809431-(Trifluoroacetyl)piperidin-4-one

Produkt 1

HCID 22643448HCID 22643448, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 10129899Acetic acid methanolLösungsmittel

Versuchsvorschrift

Methanol (150 ml) was added to an Erlenmeyer flask and acetic acid was added under stirring until pH 5. 4-Methylbenzylamine (3.14 g, 25.9 mmol) and N-trifluoroacetyl-4-piperidone (from reaction step 1) (5.065 g, 25.9 mmol) were added to a 250 ml round-bottomed flask and dissolved in the methanol/acetic acid (150 ml) solution previously made. The reaction mixture was stirred for 5 min and NaCNBH3 (2.46 g, 38.9 mmol) was added slowly under stirring. After 20 hours the reaction was concentrated and transferred to a reparatory funnel containing dichloromethane and distilled water. The aqueous phase was made basic by addition of Na2CO3. The aqueous phase was extracted twice with dichloromethane. The combined organic layers were collected and dried with Na2SO4. Concentration afforded, 4-(4-methylbenzylamine)-1-(trifluoroacetyl) piperidine. UV/MS 60/53 (M+ 301), tr (A, MS) 3.267.

Aufarbeitung

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 5 min
  3. stirringunder stirring
  4. concentrationAfter 20 hours the reaction was concentrated
  5. customtransferred to a reparatory funnel
  6. additioncontaining dichloromethane
  7. distillationdistilled water
  8. additionThe aqueous phase was made basic by addition of Na2CO3
  9. extractionThe aqueous phase was extracted twice with dichloromethane
  10. customThe combined organic layers were collected
  11. dry with materialdried with Na2SO4
  12. concentrationConcentration
  13. customafforded

Quellen und Nachweise

ORD-Eintrag
ord-61c53632a2904fda99557544afcad542
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296694B2

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