[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:15]([CH3:17])[CH3:16])[C:13]#N)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([N-][CH:22]([CH3:24])[CH3:23])(C)C.[Li+].C([Li])C[CH2:28][CH3:29].C(NC(C)C)(C)C.C(=[O:44])CCCCC.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:15]([CH3:17])[CH3:16])[C:13](=[O:44])[CH2:28][CH2:29][CH2:24][CH2:22][CH3:23])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1A solution of 2-[1-(4-chlorophenyl)cyclobutyl]-2-dimethylaminoacetonitrile (15 g prepared as described in Example A) in dry tetrahydrofuran (50 ml) was added with stirring at -70° C. over a period of 35 minutes to a solution of lithium diisopropylamide [prepared by the addition of a 2.7M solution of butyllithium in hexane (37 ml) to a solution of diisopropylamine (15 ml) in dry tetrahydrofuran (45 ml) at 5° C.] followed by stirring for 1 hour at a temperature below 5° C. A portion (ca. 100 ml) of the above solution was cooled to -70° C. A solution of hexanal (12 ml) in dry tetrahydrofuran (20 ml) was added over 10 minutes and the mixture stirred for 1 hour at -70° C. The temperature was maintained at -70° C. whilst excess saturated ammonium chloride solution was added and the mixture was then allowed to warm to ambient temperature. The mixture was extracted with ether and the dried extract evaporated to give an oil which was distilled (160°-170° C./1 mm Hg) eliminating hydrogen cyanide. The distillate was dissolved in excess 2N hydrochloric acid to give an aqueous solution which was washed with ether, basified and extracted with ether. The extract was dried and the solvent removed by evaporation to give an oil which was distilled in a Buchi Kugelrohr apparatus (250°/1 mm) to give 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylaminoheptan-2-one.
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