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

HRID 457355Notes

Reaction equation

HRID 457355 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 80041-PenteneSolvent

Conditions

Temperature
60 °C

Procedure

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 2 g 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, 8H), 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.

Workup

  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 2 g 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

Sources & evidence

ORD record
ord-45e315af268c4b8d95f53fe509e7e9dc
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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