反应详情

温度

60 °C

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.

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