Hydrochloric Acid → N-[2-(2-Methoxyphenoxy)ethyl]-N-methyl-1,3-propanediamine

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Reaction Steps

12.9 g (0.0268 mol) of N-[2-(2-methoxyphenoxy)ethyl]-N-methyl-N'-(triphenylmethyl)-1,3-propanediamine and 250 ml of methanol are introduced into a 1 l round-bottomed flask. A stream of gaseous hydrochloric acid is passed for 15 min while cooling with a mixture of water and ice. The mixture is allowed to return to room temperature and is then brought to the reflux temperature for 7.5 h. The mixture is concentrated to dryness and the residue is taken up in ethanol and concentrated again. The residue is taken up in water, the mixture is basified, the supernatant oil is taken up in dilute hydrochloric acid and extraction is carried out with diethyl ether. The acidic aqueous phase is then treated with sodium hydroxide until the pH is basic and extraction is carried out with dichloromethane. The organic phase is washed with water, dried over sodium sulphate and concentrated under reduced pressure. There are obtained 5.6 g of a yellow oil which is used as is in the following stage.

Provenance & Evidence