Chloroform → [(1,3-Diphenyl-5-propylpyrazol-4-yl)methyl]butylamine

HRID 1643189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643189
S(Cl)(Cl)=O.[C:5]1([N:11]2[C:15]([CH2:16][CH2:17][CH3:18])=[C:14]([CH2:19]O)[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(Cl)(Cl)Cl>C=CCCC>[C:5]1([N:11]2[C:15]([CH2:16][CH2:17][CH3:18])=[C:14]([CH2:19][NH:11][CH2:5][CH2:6][CH2:7][CH3:8])[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 227280971,3-Diphenyl-4-hydroxymethyl-5-propylpyrazole

Produkt 1

HCID 20777201[(1,3-Diphenyl-5-propylpyrazol-4-yl)methyl]butylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80041-PenteneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Thionyl chloride (1 mL) is added to a solution of 165 (289 mg) in pentene stabilized chloroform (8 mL) and the mixture heated to 60° C. for 2 hours. The resulting mixture is cooled, washed with saturated sodium bicarbonate solution, dried (Na2SO4), and concentrated. The resulting crude chloride is taken up in dimethylformamide (3 mL) and added dropwise to a solution of butylamine (1.0 g) in dimethylformamide (10 mL) containing 2g of powdered potassium carbonate. After the addition is complete, the resulting mixture is stirred for an additional 3 h and partitioned between water (20 mL) and ether (10 mL). The ether layer is washed 2 times with water, dried (Na2SO4), and concentrated. The resulting material is purified by chromatography on silica eluting with 10% CH3OH/CHCl3 to give the desired secondary amine 166. LC-MS (M+1): 348.3; 1H NMR (δ, CDCl3), 7.87 (dd, J=8.0, 1.6 Hz, 2H), 7.32-7.48 (m, 1H), 3.77 (s, 2H), 2.70 (m, 4H), 1.48 (m, 4H), 1.34 (m, 2H), 0.91 (t, J=7.6 Hz, 3H), 0.87 (t, J=7.6 Hz, 3H) ppm.

Aufarbeitung

  1. temperatureThe resulting mixture is cooled
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. additionadded dropwise to a solution of butylamine (1.0 g) in dimethylformamide (10 mL)
  6. additioncontaining 2g of powdered potassium carbonate
  7. additionAfter the addition
  8. custompartitioned between water (20 mL) and ether (10 mL)
  9. washThe ether layer is washed 2 times with water
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated
  12. customThe resulting material is purified by chromatography on silica eluting with 10% CH3OH/CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-ef1ed9e2ca9f4445b336282970718468
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119665B2

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