Reaktion #1914697

Reaktionsgleichung

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

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

magnesium sulfate

sodium borohydride

→

title compound

Ausbeute 71.3%

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

Ausbeute 71.3%

Lösungsmittel

methylene chloride

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationwas filtered
2. 2
   Einengenconcentrated
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
   Einengenat 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
   ExtraktionThe mixture was extracted with methylene chloride
9. 9
   Trocknenthe organic layer was dried (magnesium sulfate)
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated

Vorschrift

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)+

Quelle