3 Dimethylaminoethanol 3 Dimethylaminoethyl chloride

A solution of 21.7 g (0.11 mole) 1-adamantanecarboxylic acid chloride in 100 ml ether was added to a solution of 19.4 g (0.22 mole) 2-dimethylaminoethanol in 200 ml ether. The reaction mixture was stirred overnight at room temperature. Then additional 15.0 g (0.17 mole) 2-dimethylaminoethanol was added and the reaction mixture again stirred overnight. The reaction mixture was poured into 300 ml water and treated with 20 ml of 10% NaOH solution. From the ether layer was recovered 23.0 g of 2-dimethylaminoethyl 1-adamantanecarboxylate as oil. 

In addition 3-methylmorphol was condensed with /kdimethylamino-ethyl chloride to give 3-methyl-4-(/3-dimethylaminoethyl)-morphol [xxxvn], which was unaffected by sodium ethoxide at 150° C., but was degraded to 3-methyl-4-acetylmorphol [xxvn, R = Ac] and /S-dimethyl-aminoethanol on heating with acetic anhydride, and to morphol [xxi], /3-dimethylaminoethanol, and tetramethylethylenediamine on heating with hydrogen chloride [52],... 

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