[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11](=O)[CH3:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[ClH:14].C(N)C.C([N:20]([CH2:23][CH3:24])CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClCCl.C(OCC)C.CO>[ClH:14].[CH3:12][CH:11]([CH2:24][CH2:23][NH2:20])[CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1In dichloromethane (50 ml) was combined 1-(3-nitrophenyl)propan-2-one (1.44 grams, 8 mmole), ethylamine hydrochloride (0.42 grams, 8 mmole), and triethylamine (1.1 ml, 11 mmole). The mixture was stirred under nitrogen at room temperature for 30 minutes. Then sodium triacetoxyborohydride (2.5 grams, 11.7 mmole) was added in one portion. The mixture was stirred under nitrogen 18 hours. Additional ethylamine hydrochloride (0.4 grams) was added. After another 18 hours the mixture was diluted with ethyl ether, washed with 10% sodium hydroxide solution (50 ml), dried over anhydrous magnesium sulfate and the solvent removed under vacuum to give an oil. This oil was taken up into methanol, acidified with 1M hydrochloric acid in ether and the salt was precipitated by further addition of ether. The resulting solid was filtered and air dried to give [2-(1-methyl-2-(3-nitrophenyl)ethyl]ethylamine hydrochloride (1.4 grams, 85%), m.p. 173-175° C., M+H 208.
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