Acetic Acid → (4-Tert-butyl-benzyl)-[2-(2-chloro-pyridin-4-yl)-ethyl]-amine

HRID 19784

Reaktionsgleichung

Reaktionsgleichung von HRID 19784
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[CH:9])[CH:5]=[CH:4][N:3]=1.[C:10]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C.[OH-].[Na+]>[C:10]([C:14]1[CH:15]=[CH:16][C:17]([CH2:18][NH:19][CH2:9][CH2:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)=[CH:20][CH:21]=1)([CH3:13])([CH3:11])[CH3:12]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 27356554-tert-ButylbenzylamineHCID 5003444Sodium cyanoborohydrideHCID 234368312-Chloro-4-ethynylpyridine

Produkt 1

HCID 86613990(4-Tert-butyl-benzyl)-[2-(2-chloro-pyridin-4-yl)-ethyl]-amineAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 1.386 g of 2-chloro-4-ethynyl-pyridine (10.07 mmol), 2.65 ml of 4-tert-butyl-benzylamine (15.11 mmol), 0.58 ml of acetic acid (10.07 mmol) and 666 mg of sodium cyanoborohydride (95% purity, 10.07 mmol) in ethanol (12 ml) were heated to 105° C. in a sealed tube for 2 d. The reaction mixture was allowed to cool to RT, diluted with 3N NaOH solution and extracted with DCM. The combined organic extracts were washed with saturated NaHCO3 solution and brine, dried (Na2SO4), filtered and concentrated in vacuo. After column chromatography (heptane/EtOAc 100:0 to 0:100) 1.688 g (55%) of the title compound were isolated as a brown liquid. MS (ISP) 303.2 (M+H)+.

Aufarbeitung

  1. temperatureto cool to RT
  2. extractionextracted with DCM
  3. washThe combined organic extracts were washed with saturated NaHCO3 solution and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ebe208f56ec54742a4158767aa63b045
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745477B2

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