Water → 1-Phenylcyclohexylamine

Participants

Reaction Conditions

Reaction Steps

The crude azide (18.0 g, ≤96 mmol) was dissolved in dioxane (300 mL) with triphenylphosphine (40 g, 152 mmol) and the stirred solution was refluxed for 4 h. under N2 (g) before adding H2O (9 mL, 0.5 mol). After about 46 h. further reflux, solvent was removed in vacuo at about 45-50° C. and residual moisture was removed by azeotropic distillations in vacuo with CH3CN and Et2O, respectively. The syrupy residue was dissolved in boiling Et2O and chilled to about 0° C. for about 16 h. Precipitated Ph3PO was removed by filtration, and 1M HCl in Et2O (90 mL) was added dropwise at about 5° C. to the etherol filtrate to precipitate the desired 1-phenyl-cyclohexylamine as its HCl salt (12.7 g, LC-MS m/z 162 (MH+)) which was recrystallized from CHCl3 /i-Pr2O before use.

Provenance & Evidence