C. Botteghi et al. / Tetrahedron 57 (2001) 1631±1637
1637
2.23±2.10 (m, 2H), 1.90±1.73 (m, 2H). IR (KBr) (cm21):
3360, 3041, 2939, 2868, 1603, 1507, 1223, 1158, 827. MS
(70 eV) m/z (relative intensity): 262 (M1, 7). Anal. Calcd
for (FC6H4)2CHCH2CH2CH2OH: C, 73.27; H, 6.15. Found:
C, 73.54; H, 6.17.
1H NMR (CDCl3): d 7.83±6.92 (m, 11H), 3.92±3.82 (t, 1H,
J0.6 Hz), 2.85±2.70 (br d, 4H), 2.52±2.27 (m, 4H), 2.18±
1.95 (m, 2H), 1.79±1.40 (m, 5H). MS (70 eV) m/z (relative
intensity): 523 (M1, 14). Anal. Calcd for (FC6H4)2CHCH2
CH2CH2N(CH2)4C(OH)C6H3(Cl)(CF3): C, 63.10; H, 5.69;
N, 2.73. Found: C, 62.9; H, 5.67; N, 2.72.
4.1.10. Synthesis of 4,4-bis(p-¯uorophenyl)butylbromide
(15). A solution of 1.5 g (5.7 mmol) of PPh3 in 6 mL of
anhydrous CH3CN was cooled to 08C under nitrogen and
added dropwise with 0.91 g (5.7 mmol) of Br2 maintaining
the temperature below 58C. The mixture was then warmed
to rt and 1.0 g (3.6 mmol) of alcohol 14 dissolved in 2 mL of
CH3CN was added dropwise. The solution was left to react
for 2 h at rt and after evaporation of the solvent at reduced
pressure the product was diluted with hexane. The solid
residue was ®ltered off, the solvent evaporated and the
crude oil was puri®ed by ¯ash chromatography on silica
gel using a 7:3 hexane/ether mixture as eluent. Pure bromide
15 was obtained as a pale yellow oil in 80% yield.
Acknowledgements
We thank Dr Claudete Justina Valduga for the partial
experimental assistance.
References
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2. A search using Beilstein on line showed that about 300 known
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1H NMR (CDCl3): d 7.22±7.12 (m, 4H), 7.07±6.92 (m, 4H),
3.97±3.85 (t, 1H, J0.6 Hz), 3.48±3.38 (t, 2H, J7.3 Hz),
2.22±2.10 (m, 2H), 1.94±1.72 (m, 2H). IR (KBr) (cm21):
3046, 2926, 2863, 1597, 1506, 1221, 823. MS (70 eV) m/z
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4.1.11. Synthesis of Fluspirilen (1). A solution of 1.0 g
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625 mg (2.7 mmol) of the piperidino derivative 16, 497 mg
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1H NMR (CDCl3): d 7.30±6.85 (m, 13H), 4.74 (s, 2H),
3.94±3.89 (t, 1H, J0.6 Hz), 2.77±2.57 (m, 6H), 2.47±
2.42 (t, 2H, J7.3 Hz), 2.09±2.02 (q, 2H, J7.3 Hz),
1.74±1.70 (d, 2H, J7.3 Hz), 1.56±1.35 (m, 2H). MS
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4.1.12. Synthesis of Pen¯uridol (2). Following the pro-
cedure described for the synthesis of 1, Pen¯uridol 2 was
obtained as a white solid in 75% yield by reacting bromide
15 with the piperidino derivative 17 in boiling toluene and
in the presence of Na2CO3 and a few crystals of KI.
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