4-(Trifluoromethyl)benzylamine → HCID 22458245, compound

Participants

Reaction Steps

4-Carboxymethyl-1-tert-butoxycarbonylpiperidine (207 mg, 0.85 mmol, commercially available from Neosystem), 1-(3-(N,N-dimethylamino)-prop-1-yl)-3-ethylcarbodiimide hydrochloride (EDC) (177 mg, 0.92 mmol) and 4-(N,N-dimethylamino)pyridine (2 mg, 0.02 mmol) were dissolved in 4 mL of CH2Cl2. (4-(Trifluoromethyl)benzyl)amine (0.114 mL, 0.8 mmol) was added and the reaction was stirred at rt for 14 h. The mixture was diluted with CH2Cl2, washed with 1 N NaOH, 1 N HCl and brine and dried over MgSO4. The solvent was removed, the residue was redissolved in 1% HCl/methanol and the solution was heated to 50° C. for 24 h. The solution was then concentrated to afford 208 mg (77%) of the title compound. ESI-MS: 301.1 (M+H); HPLC A: 1.66 min.

Provenance & Evidence