[C:1]([O:5]CC)(=O)[CH:2]=[CH2:3].[CH3:8][N:9]([CH3:15])[CH2:10][CH2:11][CH2:12][NH:13][CH3:14].[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>C(OCC)(=O)C.CCOCC>[CH3:8][N:9]([CH3:15])[CH2:10][CH2:11][CH2:12][N:13]([CH3:14])[CH2:3][CH2:2][CH2:1][OH:5]
Under stirring, 15 g. ethyl acrylate was added to 11.6 g. N,N,N'-trimethyl-propane-1,3-diamine. Stirring was continued 8 hours at room temperature and the mixture was then heated to 80° C. for 16 hours before stripping the solvent in vacuo. The residue was dissolved in 75 ml. ether and added to a slurry of 2.1 g. LiAlH4 in 100 ml. of ether. This mixture was refluxed 2 hours. After cooling, ethyl acetate and then aqueous HCl were added and the mixture was stirred one hour. The clear, two-phase system was separated. The organic layer was dried over MgSO4, filtered, stripped of solvent, and the residue was distilled at 70°-75° C./0.4 mm, producing pure N,N,N'-trimethyl-N'-(3-hydroxypropyl)propane-1,3-diamine.
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