Reaktion #164137

Reaktionsgleichung

acetic acid

title compound

{4-[(benzyl-methyl-amino)-methyl]-1,4-diphenyl-cyclohexyl}-methylamine

formalin

sodium cyanoboron hydride

→

[4-[(benzyl-methyl-amino)-methyl]-1,4-diphenyl-cyclohexyl]-dimethylamine

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was subsequently stirred for 45 min at room temperature
2. 2
   SonstigeFor work up the solvent was removed in a vacuum
3. 3
   Extraktionextracted with ether (3×40 mL)
4. 4
   TrocknenThe organic solution was dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated to low volume in a vacuum
7. 7
   SonstigeThe remaining residue was purified by Chromatotron and with cyclohexane/ethyl acetate 1:1
8. 8
   SonstigeSeparation of the diastereomers could not

Vorschrift

A solution of the title compound from step 10 (diastereomer mixture) (0.350 g, 0.878 mmol) and formalin (1.23 mL, 37% aqueous solution) in acetonitrile (15 mL) was mixed in portions with sodium cyanoboron hydride (0.250 g, 3.86 mmol) and stirred for 45 min at room temperature. Conc. acetic acid was then added until a neutral reaction occurred and the mixture was subsequently stirred for 45 min at room temperature. For work up the solvent was removed in a vacuum, the residue taken up in 2N NaOH (40 mL) and then extracted with ether (3×40 mL). The organic solution was dried over Na2SO4, filtered and concentrated to low volume in a vacuum. The remaining residue was purified by Chromatotron and with cyclohexane/ethyl acetate 1:1. Separation of the diastereomers could not be achieved.

Quelle