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Reference Example 9 5-Fluoro-6-methoxy-1-indanone In the same manner as in Reference Example 6, the target compound was obtained from 3-(3-fluoro-4-methoxyphenyl)propionic acid. The yield was 91percent. m.p.: 152-153° C. (recrystallized from methanol/ethyl acetate); NMR (CDCl3) delta: 2.71 (2H, t, J=5.7 Hz), 3.08 (2H, t, J=5.7 Hz), 3.92 (3H, s), 7.17 (1H, d, J=10.3 Hz), 7.29 (d, J=8.1 Hz); Elemental Analysis for C10 H9 FO2: Calcd.: C 66.66; H 5.03; Found: C 66.82; H 5.06
A mixture of Compound II (900 mg), toluene (9 mL) and thionyl chloride (393 muL) was stirred at 90° C. for one hour, and concentrated under reduced pressure. The obtained residue was added to an ice-cold solution of aluminium chloride (605 mg) in methylene chloride (45 mL), and the mixture was stirred for one hour. The reaction solution was added dropwise into ice-cold water, and the mixture was stirred for one hour, ane extracted with ether. The organic layer was washed with aqueous sodium bicarbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to give Compound III (666 mg).
Reference Example 10 (E)-(5-fluoro-6-methoxyindan-1-ylidene) acetonitrile In the same manner as in Reference Example 7, the target compound was obtained from <strong>[83802-71-5]5-fluoro-6-methoxy-1-indanone</strong> and diethyl cyanomethylphosphonate. The yield was 75percent. m.p.: 197-199° C. (recrystallized from hexane/ethyl acetate); NMR (CDCl3) delta: 3.00-3.19 (4H, m), 3.92 (3H, s), 5.53 (1H, t, J=2.2 Hz), 7.02 (1H, d, J=7.6 Hz), 7.07 (1H, d, J=10.3 Hz); Elemental Analysis for C12 H10 FNO: Calcd.: C 70.93; H 4.96; N 6.89; Found: C 70.65; H 5.13; N 6.99
Example 4 4-(6-fluoro-indan-1-yl)piperidine This compound was prepared in two steps from 4-bromopyridine and <strong>[83802-71-5]5-fluoro-6-methoxy-1-indanone</strong> as described in method 2 above to give the product as the HCl salt (66percent, mp: 178°-179° C.). Anal. Calc'd for C15 H2 FNOodsold;HCl: C, 63.04percent; H, 7.41percent; N, 4.90percent. Found: C, 62.80percent; H, 7.30percent; N, 4.70percent.
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