[O:1]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][NH:4][C:3](=[O:12])[CH2:2]1.I[CH2:14][CH2:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:18].O>CN(C)C=O.C(N(CC)CC)C>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:17]([CH2:16][CH2:15][CH2:14][N:9]2[CH2:8][CH2:7][C:6]3([O:1][CH2:2][C:3](=[O:12])[NH:4][CH2:5]3)[CH2:11][CH2:10]2)=[O:18])=[CH:24][CH:23]=1A solution of 2.5 g of 1-oxa-4,9-diazaspiro[5.5]undecan-3-one and 5 ml of 4-iodo-p-fluorobutyrophenone in 60 ml of dimethylformamide and 10 ml of triethylamine was heated at 60° C. for 10 hours. The mixture was poured into water, extracted with methylene chloride, and the methylene chloride layer was extracted with aqueous 5% HCl. Basification of the aqueous extract with ammonium hydroxide and extraction with methylene chloride followed by evaporation gave a residue which was crystallized from ethyl acetate-hexane to give 9-[3-(4-fluorobenzoyl)propyl]-1-oxa-4,9-diazaspiro[5.5]undecan-3-one, m.p. 117°-118° C. The HCl salt of 9-[3-(4-fluorobenzoyl)propyl]-1-oxa-4,9-diazaspiro[5.5]undecan-3-one was prepared by dissolving the base in methanolic HCl and precipitating with ether, m.p. 225°-230° C.
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