Reaktion #721943

ord-ce0d06d9214a462da7dc46f2ede5e1db

Reaktionsgleichung

c1ccc(CCCN[C@H]2CC[C@H](c3ccc(OCc4ccccc4)cc3)CC2)cc1
trans-[4-(4-benzyloxy-phenyl)-cyclohexyl]-(3-phenyl-propyl)-amine
→
Oc1ccc([C@H]2CC[C@H](NCCCc3ccccc3)CC2)cc1
trans-4-[4-(3-phenyl-propylamino)-cyclohexyl]-phenol
Ausbeute 84.0%

Edukte

c1ccc(CCCN[C@H]2CC[C@H](c3ccc(OCc4ccccc4)cc3)CC2)cc1
trans-[4-(4-benzyloxy-phenyl)-cyclohexyl]-(3-phenyl-propyl)-amine

Reagenzien

[Pd]
Pd/C

Lösungsmittel

CO
MeOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeRemoval of the catalyst and evaporation of the solvent
  2. 2
    workup.WAITleft a residue which after trituration with ether

Vorschrift

A mixture of trans-[4-(4-benzyloxy-phenyl)-cyclohexyl]-(3-phenyl-propyl)-amine (200 mg, 0.5 mmol), Pd/C 10% (20 mg) and MeOH (20 ml) was hydrogenated at RT for 3 h. Removal of the catalyst and evaporation of the solvent left a residue which after trituration with ether gave trans-4-[4-(3-phenyl-propylamino)-cyclohexyl]-phenol (130 mg, 84%) as a white crystalline material. MS: m/e=310.3 (M+H+).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06184236B2uspto-grants-2001_02