반응 #1914697

반응 방정식

2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde

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

magnesium sulfate

sodium borohydride

→

title compound

수율 71.3%

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

수율 71.3%

용매

methylene chloride

methanol

반응 조건

후처리

1. 1
   여과was filtered
2. 2
   농축concentrated
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 25 mL of 2:1 (v/v) ethanol
4. 4
   workup.ADDITIONadded over 1 hr
5. 5
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 2 hr
6. 6
   농축at which time it was concentrated to one-half of its original volume
7. 7
   workup.ADDITIONTo this mixture was added 25 mL water and 25 mL saturated aqueous sodium bicarbonate
8. 8
   추출The mixture was extracted with methylene chloride
9. 9
   건조the organic layer was dried (magnesium sulfate)
10. 10
    여과filtered
11. 11
    농축concentrated

실험 절차

To a solution of 2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (1.68 g, 6.97 mmol) and 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (1.37 g, 6.64 mmol) in 25 mL methylene chloride was added magnesium sulfate (2.81 g, 23.3 mmol). The reaction mixture was stirred under nitrogen at room temperature overnight, then was filtered, and concentrated. The residue was dissolved in 25 mL of 2:1 (v/v) ethanol:methanol and was treated with sodium borohydride (1.51 g, 39.84 mmol) in portions added over 1 hr. The reaction mixture was stirred at room temperature for 2 hr. at which time it was concentrated to one-half of its original volume. To this mixture was added 25 mL water and 25 mL saturated aqueous sodium bicarbonate. The mixture was extracted with methylene chloride and the organic layer was dried (magnesium sulfate), filtered, and concentrated. Medium pressure silica gel chromatography of the residue (methylene chloride to 10% methanol/methylene chloride) afforded 2.04 g (71%) of the title compound. MS 431.1 (M+1)+

출처