[CH2:1]([Li])CCC.[CH:6]([NH:9][CH:10](C)C)(C)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2(C(N(C)C)C#N)[CH2:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1.[CH:30](=[O:32])[CH3:31].[Cl-].[NH4+]>CCCCCC.O1CCCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2([CH:31]([N:9]([CH3:10])[CH3:6])[C:30](=[O:32])[CH3:1])[CH2:23][CH2:22][CH2:21]2)=[CH:18][CH:19]=1A 1.55M solution of n-butyllithium in hexane (129 ml) was added to a stirred solution of diisopropylamine (22.3 g) in dry tetrahydrofuran (90 ml) and the resulting mixture was stirred for 30 minutes at 0° C. The mixture was then cooled to -70° C. in an acetone/dry ice bath and a solution of 2-[1-(4-chlorophenyl)cyclobutyl]-2-dimethylaminoacetonitrile (30 g prepared as described in Example A) in dry tetrahydrofuran (100 ml) was added to the reaction mixture under nitrogen over 50 minutes at -70° C. and then stirred for 11/2 hours at a temperature of less than 5° C. The mixture was then cooled to -70° C. and treated with a solution of acetaldehyde (13.6 g) in dry tetrahydrofuran (40 ml). After the mixture had been stirred for 1 hour at -70° C. under nitrogen the mixture was treated with excess saturated ammonium chloride solution and allowed to warm to 0° C. The aqueous layer was then separated and extracted with ether. The extract was combined with the organic phase of the reaction mixture, dried and the solvents removed by evaporation to give an oil which was distilled (eliminating hydrogen cyanide) (154°-160° C./5 mm Hg) to give 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylaminopropan-2-one.
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