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 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.

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