반응 #1914701

반응 방정식

magnesium sulfate

magnesium sulfate

3-methyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde

4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine

magnesium sulfate

→

title compound

수율 117.8%

[3-Methyl-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

수율 117.8%

용매

methylene chloride

반응 조건

후처리

1. 1
   여과The reaction mixture was filtered
2. 2
   농축concentrated
3. 3
   workup.DISSOLUTIONThe residue was redissolved in 20 mL methylene chloride
4. 4
   workup.WAITThe reaction was again stirred overnight at room temperature
5. 5
   여과The reaction was filtered
6. 6
   농축concentrated
7. 7
   workup.DISSOLUTIONThe residue was again redissolved in 20 mL methylene chloride
8. 8
   workup.WAITThe reaction was once again stirred overnight at room temperature
9. 9
   여과The reaction was filtered
10. 10
    농축concentrated
11. 11
    workup.DISSOLUTIONThe resulting oil was dissolved in 12 mL ethanol
12. 12
    workup.ADDITION6 mL methanol and was treated with sodium borohyride (0.560 g, 14.80 mmol) which
13. 13
    workup.ADDITIONwas added in two portions over a period of 1 hr
14. 14
    workup.STIRRINGThe reaction was stirred at room temperature for 4 days at which time the solvent
15. 15
    기타was removed in vacuo
16. 16
    workup.ADDITIONTo the residue was added water
17. 17
    추출the mixture was extracted three times with methylene chloride
18. 18
    세척The combined organic layers were washed with saturated aqueous sodium chloride
19. 19
    건조dried (sodium sulfate)
20. 20
    여과filtered
21. 21
    농축concentrated

실험 절차

To a solution of 3-methyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (0.700 g, 3.18 mmol) and 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (0.624 g, 3.02 mmol) in 20 mL methylene chloride was added magnesium sulfate (1.82 g, 15.12 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was filtered and concentrated. The residue was redissolved in 20 mL methylene chloride and was treated with magnesium sulfate (1.82 g, 15.12 mmol). The reaction was again stirred overnight at room temperature. The reaction was filtered and concentrated. The residue was again redissolved in 20 mL methylene chloride and was treated with magnesium sulfate (1.82 g, 15.12 mmol). The reaction was once again stirred overnight at room temperature. The reaction was filtered and concentrated. The resulting oil was dissolved in 12 mL ethanol and 6 mL methanol and was treated with sodium borohyride (0.560 g, 14.80 mmol) which was added in two portions over a period of 1 hr. The reaction was stirred at room temperature for 4 days at which time the solvent was removed in vacuo. To the residue was added water, and the mixture was extracted three times with methylene chloride. The combined organic layers were washed with saturated aqueous sodium chloride, dried (sodium sulfate), filtered, and concentrated to afford 1.46 g of the title compound. MS 411.4 (M+1)+

출처