[CH2:1]([NH:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCOCCOC.[S:21](=O)(=[O:24])([OH:23])[OH:22].CO>O.C1(C)C=CC=CC=1>[S:21]([OH:24])([O:11][CH2:10][CH2:9][NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:23])=[O:22]To a solution of N-benzylethanolamine (302 g) in a mixture of water (8.92 ml) and toluene (1510 ml) and diglyme (151 ml) was added dropwise sulfuric acid (128 ml) over 30 minutes, and the mixture was stirred under reflux for 6 hours. After cooled to room temperature, to the mixture was added methanol (300 ml), and then the mixture was stirred for 1 hour. The precipitate was filtered and washed with methanol (300 ml×4), and dried to give 2-(N-benzylamino)ethyl hydrogen sulfate (352.6 g) as a white powder.
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