Sodium Iodide → HCID 59803210, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of sodium iodide (0.19 mL, 4.6 mmol), trans-N1,N2-dimethylcyclohexane-1,2-diamine (0.034 g, 0.24 mmol), (R)—N-(3-bromo-4-chlorobenzyl)-1-phenylethanamine 75 (0.762 g, 2.3 mmol), and copper(I) iodide (0.025 mg, 0.13 mmol) was added in dioxane (2.5 mL). The reaction mixture was degassed by bubbling nitrogen through the solution for 5 min and heated to 115° C. in a sealed tube. After 15 h, the reaction mixture was diluted with EtOAc and the organic phase was washed with dilute NH4OH (1×), brine (1 x), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 10% to 40% EtOAc in hexanes) gave (R)—N-(4-chloro-3-iodobenzyl)-1-phenylethanamine 77 (0.737 g, 84% yield) as a colorless oil. Mass spectrum: calculated for C15H15ClIN 371.0. found 372.1 (M++1).

Provenance & Evidence