S(O)(O[CH2:5][CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)=O.[CH3:16][O:17][CH2:18][C:19]1([CH2:22][O:23][CH3:24])[CH2:21][O:20]1>O.[OH-].[Na+]>[CH2:8]([N:7]1[CH2:6][CH2:5][O:20][C:19]([CH2:18][O:17][CH3:16])([CH2:22][O:23][CH3:24])[CH2:21]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1To a solution of 2-(N-benzylamino)ethyl hydrogen sulfate (28 g) in a mixture of water (36.3 ml) and 40% sodium hydroxide aqueous solution (12.1 ml) was added 2,2-bis(methoxymethyl)oxirane (16.0 g) at room temperature over 30 minutes. After stirring at room temperature for 87 hours, 40% sodium hydroxide aqueous solution (73 ml) was added dropwise to the mixture over 20 minutes. The mixture was stirred at room temperature for 1 hour and at 40° C. for 20 hours, and extracted with ethyl acetate (100 ml×3). The organic layer was extracted with 1N hydrochloric acid (×6). The combined extracts were neutralized with sodium hydroxide, and then added sodium chloride, and extracted with ethyl acetate (100 ml×3). The combined extracts were washed with brine, dried over magnesium sulfate, and evaporated under reduced pressure to give 4-benzyl-2,2-dimethoxymethylmorpholine (31.79 g) as an orange oil.
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