Methyl iodide → 6-(4-Chlorophenoxy)-1-methyl-hexylamine

Participants

Reaction Conditions

Reaction Steps

Magnesium (120 mg, 5 mmol) was added to Et2O (15 mL), followed by Methyl iodide (310 μl, 5 mmol). After reflux has ceased, the mixture was heated to reflux for 20 min. The solution was than cooled to 0° C. and 6-(4-chloro-phenoxy)-hexanenitrile (1119 mg, 5 mmol) was added. The ice bath was removed and the mixture was stirred at ambient temperature for 20 h. The mixture was then diluted with dry THF (5 mL) ad cooled to −78° C. NaBH4 (190 mg, 5 mmol) was added followed by MeOH (3.5 ml) and stirring was continued at −78° C. for 4.5 h. The reaction was quenched by careful addition of 1M aqueous HCl (20 mL). The layers were separated, the aqueous layer was washed with Et2O (1×25 mL), the organic layer was extracted with 1M aqueous HCl (3×30 mL). The aqueous layers were adjusted to pH 12 by addition of 10M aqueous NaOH (8 mL) and extracted with EtOAc (3×50 mL). The combined org. layers were dried over Na2SO4, filtered and the solvent was removed under reduced pressure to give the title compound (ca 30% of total by integration of HPLC trace at 218 nm) together with two more hydrophobic byproducts (total: 766 mg).

Provenance & Evidence