[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]23[CH2:12][CH:11]2[CH2:10][NH:9][CH2:8]3)=[CH:3][CH:2]=1.[CH2:14](I)[CH3:15].C(=O)([O-])[O-].[Na+].[Na+].[ClH:23]>CCOCC.C1(C)C=CC=CC=1>[ClH:23].[CH2:14]([N:9]1[CH2:10][CH:11]2[C:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:13])=[CH:6][CH:5]=3)([CH2:12]2)[CH2:8]1)[CH3:15]A mixture of 7.4 g. of 1-(p-tolyl)-3-azabicyclo[3.1.0]hexane (Example 32), 7.3 g. of ethyl iodide and 8.9 g. of sodium carbonate in 60 ml. of toluene is heated at reflux for 18 hrs. Filtration and evaporation of this mixture gives a residue which is dissolved in ether. Addition of ethanolic hydrogen chloride gives a precipitate which is recrystallized from acetonitrile to give the desired product as colorless crystals, m.p. 175°-176° C.
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