1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (+)-4-Phenyl4-[(1-(3,5-bis(trifluoromethyl)phenyl)-2-hydroxyethoxy)methyl]-1-(2-(pyrrolidinyl)acetamido)piperidine Hydrochloride

Participants

Reaction Steps

1-[3-Dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride (797 mg), hydroxybenzo-triazole trihydrate (475 mg) and triethylamine (0.890 ml) were added to a stirred solution of 2-pyrrolidinyl acetic acid hydrochloride (528 mg) in dry dimethylformamide at room temperature. After 30 minutes a solution of the compound of Example 14 (800 mg) in dry dimethylformamide was added, followed by triethylamine (0.590 ml). The resulting solution was stirred at room temperature for 4 hours. The reaction was quenched with water and extracted into diethyl ether then the organic solution was dried (MgSO4) and evaporated to give a yellow oil. The residue was purified by chromatography on grade 3 neutral alumina (1% methanol/dichloromethane) then treated with ethereal hydrogen chloride to afford the title compound, mp=106°-108° C.;

Provenance & Evidence