B.CSC.[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]2[O:17][CH2:16][C:15](=O)[N:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:13]2)[CH:9]=[CH:10][CH:11]=1.CO.Cl>O1CCCC1>[ClH:5].[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]2[O:17][CH2:16][CH2:15][N:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:13]2)[CH:9]=[CH:10][CH:11]=1Borane-methyl sulphide (0.5 ml) was added dropwise, under nitrogen, to a stirred solution of 2-[3-chlorophenyl]-4-[1,1-dimethylethyl]-5-oxomorpholine (0.85 g) in dry tetrahydrofuran (40 ml). The mixture was heated under reflux for 2 h., cooled, treated with methanol (5 ml) and heated for 1 hr. The resulting solution was cooled, treated with hydrogen chloride and evaporated to give 2-[3-chlorophenyl]-4-[1,1-dimethylethyl]morpholine hydrochloride as a white solid (0.54 g), m.p. 223°-8° C. (ethyl acetate).
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