Reaktion #164129

Reaktionsgleichung

acetic acid

title compound

[1-(4-methoxyphenyl)-4-methylamino-4-phenyl-cyclohexyl]-dimethylamine

formalin

sodium cyanoboron hydride

→

[4-dimethylamino-1-(4-methoxyphenyl)-4-phenyl-cyclohexyl]-dimethylamine

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred for 45 min at RT
2. 2
   SonstigeFor work up the solvent was removed in a vacuum
3. 3
   Extraktionextracted with ether (3×10 mL)
4. 4
   TrocknenThe organic solution was dried over Na2SO4
5. 5
   Einengenconcentrated to low volume in a vacuum
6. 6
   SonstigeThe remaining residue was purified by means of flash chromatography with ethyl acetate/methanol (2:1→1:1→1:1+2% NH3)

Vorschrift

A solution of the title compound from Example 68 (96 mg, 0.28 mmol) and formalin (0.39 mL, 37% aqueous solution) in acetonitrile (3 mL) was mixed with sodium cyanoboron hydride (72 mg, 1.15 mmol) and stirred for 45 min at RT. Conc. acetic acid was then added until a neutral reaction occurred and the mixture stirred for 45 min at RT. For work up the solvent was removed in a vacuum, the residue taken up in 2N NaCl (5 mL) and then extracted with ether (3×10 mL). The organic solution was dried over Na2SO4 and concentrated to low volume in a vacuum. The remaining residue was purified by means of flash chromatography with ethyl acetate/methanol (2:1→1:1→1:1+2% NH3).

Quelle