Chloroform → HCID 131716146, compound

Participants

Reaction Steps

The filtrate residue which was saved in Illustration 4, was treated with 1 L CHCl3 and 0.9 L 5% NH4OH, shaken vigorously, the layers separated and the organic phase washed with 4×800 ml 5% NH4OH and 2×500 ml H2O, then dried over MgSO4 and evaporated to an oil 32.3 g, which is enriched in (+)-1,2-diphenyl-2-propylamine. This oil (32.3 g, 0.153 mol) was dissolved in 200 ml hot 95% ethanol and added to a stirred solution of (+)-dibenzoyl tartaric acid monohydrate (57.55 g, 0.153 mol) in 600 ml of refluxing 95% ethanol. A white solid crystallized immediately, which was stirred at reflux for 5 minutes, then allowed to cool to ambient temperature. The solid was collected by filtration and vacuum dried at 80° C. for 8 hours to give 71.6 g of (+)-1,2-diphenyl-2-propylamine (+)-dibenzoyltartrate, mp 197°-198° C., [α]D =+95.8° (C=0.5, CH3OH). 5.0 g of this salt was dissolved in 250 ml CHCl3 and 200 ml 5% NH4OH, shaken vigorously, the layers separated and the organic phase washed with 3×200 ml 5% NH4OH and 2×200 ml H2O and dried over MgSO4. The solvent was evaporated to give 1.75 g of (+)-1,2-diphenyl-2-propylamine as an oil. The maleate salt was prepared by dissolving this oil in 25 ml ethyl acetate and adding the solution to a hot solution of maleic acid (1.02 g, 8.78 mmole) in 50 ml 3/1 ethyl acetate/isopropanol. Upon cooling a white solid crystallized, which was collected by filtration and vacuum dried to give 2.06 g of (+)-1,2-diphenyl-2-propylamine maleate, mp 177°-178° C., [α]D =+27.3° (C=1, CH3OH).

Provenance & Evidence