Sodium Hydroxide → HCID 54570919, compound

Participants

Reaction Steps

A mixture of N-(3-hydroxypropyl)-N-[2-[phenyl(hydroxy)methyl]cyclohexyl]amine, from step (a) above, 50 g (0.19 mole) and 250 ml of concentrated hydrochloric acid was heated on a steam bath for 1.5 hr. The resulting solution was cooled in ice, basified with 20% aqueous sodium hydroxide solution and the product was extracted well with diethyl ether. The ether extract was dried with magnesium sulfate and evaporated to give 45.3 g of N-(3-hydroxypropyl)-N-[2-(phenylmethylene)cyclohexyl]amine, as an oil, which was used directly in the next preparative step. However, a portion of this amine oil was converted to its hydrochloride in methanol with a diethyl ether solution of hydrogen chloride and the salt was crystallized from the methanol/diethyl ether mixture, mp 175°-177° C. The IR, UV and NMR spectra were consistent.

Provenance & Evidence