[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:16]([CH3:18])[CH3:17])C(=O)C)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:19]([Mg]Br)[CH3:20].C(Br)C.[Mg].Cl.CC[O:30][CH2:31][CH3:32]>CC(C)=O.CC(O)C.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH:12]([N:16]([CH3:18])[CH3:17])[C:31]([CH3:32])([OH:30])[CH2:19][CH3:20])[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylaminopropan-2-one (10 g prepared as described in Example 47) in dry ether (25 ml) was added dropwise to a stirred solution of ethyl magnesium bromide prepared by the reaction of a solution of ethyl bromide (5 ml) in dry ether (20 ml) with magnesium (1.3 g) in dry ether (160 ml). The mixture was stirred for two hours at ambient temperature and water (60 ml) and then 5N hydrochloric acid (60 ml) were added. The mixture was allowed to stand for 16 hours and the aqueous layer was separated, washed with ether, basified and extracted with ether. The extract was dried and the ether removed to give an oil which was treated with a mixture of excess concentrated hydrochloric acid and propan-2-ol. Evaporation yielded a gum which was dissolved in acetone. The volume of the acetone solution was reduced and a solid precipitated which was collected and recrystallised from propan-2-ol to give 1-[1 -(4-chlorophenyl)cyclobutyl]-1-dimethylamino-2-methylbutan-2-ol hydrochloride (m.p. 167°-170° C. (dec)).
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