ClCC([N:6]=[C:7]([Cl:9])[CH3:8])CC.[Cl:10][CH2:11][CH:12]([N:15]=[C:16](Cl)[CH3:17])[CH2:13][CH3:14].O.[CH3:20][CH2:21][CH:22]([NH2:25])[CH2:23][OH:24].[OH:26]CC(NC(=O)C)CC>C(O)C.CO.C(O)(=O)C>[CH3:20][CH2:21][CH:22]([NH2:25])[CH2:23][OH:24].[C:7]([Cl:9])(=[NH:6])[CH3:8].[Cl:10][CH2:11][CH:12]([NH:15][C:16](=[O:26])[CH3:17])[CH2:13][CH3:14]Hydrolysis of N-[1-(chloromethyl)propyl]acetimidoyl chloride is highly pH dependent. It has now been found that a simple hydrolysis procedure is effective. On refluxing with water N-[1-(chloromethyl)propyl]acetimidoyl chloride is transformed into a mixture of dl-2-amino-1-butanol (77%), dl-2-amino-1-butanol acetate hydrochloride (17%), the N-[1-(hydroxymethyl)propyl]acetamide (7%) and acetic acid within 1 hour. The product ratios appear to represent equilibrium compositions because additional heating (14 hrs.) does not materially change their distribution. If, however, the hydrolysis is carried out with aqueous methanol or ethanol, it is complete within 2 hours and the acetyl component of the product can be removed as methyl or ethyl acetate by distillation. This procedure not only decreases hydrolysis time, it also avoids the accumulation of salts in the reaction mixture, gives essentially quantitative yields of dl-2-amino-1butanol from N-[1-chloromethyl)propyl]acetimidoyl chloride through N-[1-(chloromethyl)propyl]acetamide, and facilitates product work-up. Methyl acetate boils at 57° C., and is readily distilled off.
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