[Cl-].CS(C)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][OH:21])[CH2:16][CH2:15]2)=[CH:9][CH:8]=1.CCN(CC)CC>C(Cl)Cl.O>[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([CH:20]=[O:21])[CH2:16][CH2:15]2)=[CH:9][CH:8]=1
A solution of oxylyl chloride (0.59 ml, 3.95 mmol) in CH2Cl2 (20 ml) was cooled to −78° C. DMSO (0.95 ml, 13.38 mmol) was added dropwise into the oxylyl chloride solution. The reaction mixture was stirred for 5 minutes, and 1-[(4-fluorophenyl)methyl]-4-piperidinemethanol (0.99 g, 4.46 mmol) in CH2Cl2 (20 ml) was added dropwise into the reaction solution. Stirring was continued for an additional 20 minutes. Et3N, 8.0 ml was added and the reaction mixture was stirred for 10 minutes and then allowed to warm to room temperature. Water (50 ml) was added and the mixture was extracted with CH2Cl2. The combined CH2Cl2 solution was dried over Na2SO4. The evaporation of solvent gave an oil, 0.77 g (79% yield). 1H NMR (CD3Cl) δ 9.65 (1H, s, CHO), 7.30-7.24 (2H, m, Ar—H), 7.00-6.97 (2H, m, Ar—H), 3.46 (2H, s, p-FPhCH2), 2.81-2.76 (2H, m, N(CH)2), 2.30-2.20 (1H, m, CHCHO), 2.14-2.06 (2H, dt, J=2.1, 11.3 Hz, N(CH)2), 1.92-1.86 (2H, dd, J=3.5, 13.5 Hz), 1.74-1.62 (2H, m).
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