Hydrochloric Acid → HCID 178448123, compound

Participants

Reaction Steps

To a solution of 4-isopropylcyclohexanone (5.0 g, 36 mmol) and benzylamine (3.54 mL, 32 mmol) in MeOH (40 mL) was added 4 Å molecular sieves (2 g). After 16 h at rt NaBH4 (2.45 g, 65 mmol) was added and the mixture stirred for a further 6 h. Water (3 mL) was added and the solvent was removed in vacuo. The residue was partitioned between NaHCO3 (150 mL) and EtOAc (150 mL), the aqueous layer was extracted with EtOAc (2×50 mL) and the combined organic phases were washed with brine (2×50 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (SiO2, NH4OH:MeOH:DCM 0.25:5:95) to give the product as a free base. 4M HCl in dioxane and Et2O were added to the residue, and the resulting precipitate was filtered to give the title compound: δH (CD3OD) 0.92-0.97 (6H, m), 1.17-1.26 (1H, m), 1.53-1.92 (9H, m), 3.21-3.29 (1H, m), 4.23 (2H, s) 7.44-7.54 (5H, m).

Provenance & Evidence