F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[OH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:16][CH2:15]1To a 20 ml N,N-dimethylformamide solution of 1.0 g (5.95 mmol) of ethyl 4-fluorobenzoate, 662 mg (6.54 mmol) of 4-hydroxypiperidine and 1.23 g (8.92 mmol) of potassium carbonate were added, and the mixture was stirred for 24 hours at 120° C. The reaction mixture was returned to room temperature, and the solvent was distilled off under reduced pressure. Then, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. Then, the solvent was distilled off under reduced pressure. Diethyl ether was added to the residue, and precipitated crystals were collected to obtain 234 mg (16%) of the captioned compound.
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