J. T. Welch, D. S. Lim / Bioorg. Med. Chem. 15 (2007) 6659–6666
6665
(282 MHz, CDCl3, ppm) d 82.7 (AB4 (nine lines), 1F,
SF), 62.1 (d, JAB = 150.0 Hz, 4F, SF4); 13C NMR
(100 MHz, CDCl3, ppm) 154.3 (quintet,
J = 17.9 Hz), 149.5, 133.5, 132.4, 131.2, 129.4, 127.1
(quintet, J = 4.7 Hz), 127.0 (quintet, J = 4.6 Hz), 13.8.
References and notes
1. Rothman, R. B.; Baumann, M. H.; Savage, J. E.; Rauser,
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1428.
d
5.3.12. 1-(3-(Pentafluorosulfanyl)phenyl)propan-2-amine
18. To a solution of LAH (0.555 g, 13.9 mmol) in
THF (20 mL) at 0 ꢁC was slowly added 17 (0.73 g,
2.5 mmol). After heating under reflux for 1.5 h, the reac-
tion mixture was quenched at 0 ꢁC by the cautious
addition of water until hydrogen evolution ceased. After
stirring for 1 h with anhydrous MgSO4, the mixture was
filtered, washed with 10% HCl, the acid phase neutral-
ized with 10% NaOH, and then back-extracted with
dichloromethane. The combined organic layers were
dried over MgSO4, concentrated and the crude product
was purified by column chromatography to afford
0.388 g of a colorless liquid (59% yield). 1H NMR
(300 MHz, CDCl3, ppm):
d 7.63–7.50 (m, 2H),
7.42–7.26 (m, 2H), 3.25–3.08 (m, 1H), 2.72 (dd,
J = 13.4, 5.6 Hz, 1H), 2.59 (dd, J = 13.4, 7.8 Hz, 1H),
1.64 (s, 2H), 1.65 (d, J = 6.3 Hz, 3H); 19F NMR
(282 MHz, CDCl3, ppm) d 84.3 (AB4 (nine lines), 1F,
SF), 62.3 (d, JAB = 149.8 Hz, 4F, SF4); 13C NMR
13. Schiller, N. B. J. Am. Coll. Cardiology 1999, 34, 1159.
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Germany) 1979, 66, 159.
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(100 MHz,
CDCl3,
ppm)
d
154.1
(quintet,
J = 16.4 Hz), 140.7, 132.4, 128.7, 126.5 (quintet,
J = 4.5 Hz), 123.9 (quintet, J = 4.8 Hz), 48.3, 46.0,
23.2; Anal. Calcd for C9H12F5NS: C, 41.38; H, 4.63.
Found: C, 41.20; H, 4.52.
5.3.13. N-Ethyl-1-(3-(pentafluorosulfanyl)phenyl)propan-
2-amine 19. To a solution of 18 (0.069 g, 0.26 mmol) in
1,2-dichloroethane (4 mL) at room temperature was
added acetaldehyde (0.012 g, 0.40 mmol). After stirring
for 2 min, sodium triacetoxyborohydride (0.084 g,
0.40 mmol) was added and the mixture stirred for
4.5 h. On quenching with water, the reaction mixture
was extracted with three portions of chloroform. The
combined organic layers were washed with sat.
NaHCO3, dried over anhydrous MgSO4, concen-
trated, and the crude product purified by column
chromatography to afford 0.023 g of a colorless li-
26. Curzon, G.; Gibson, E. L.; Oluyomi, A. O. Trends
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1
27. Fitzgerald, L. W.; Burn, T. C.; Brown, B. S.; Patterson, J.
P.; Corjay, M. H.; Valentine, P. A.; Sun, J.-H.; Link, J. R.;
Abbaszade, I.; Hollis, J. M.; Largent, B. L.; Hartig, P. R.;
Hollis, G. F.; Meunier, P. C.; Robichard, A. J.; Robert-
son, D. W. Mol. Pharmacol. 2000, 57, 75.
quid (30% yield). H NMR (400 MHz, CDCl3, ppm):
d 7.61–7.53 (m, 2H), 7.40–7.29 (m, 2H), 3.00–2.82
(m, 2H), 2.79–2.58 (m, 3H), 2.29–1.79 (bs, 1H), 1.13–
1.01 (m, 6H); 19F NMR (282 MHz, CDCl3, ppm) d
84.3 (AB4 (nine lines), 1F, SF), 62.2 (d, JAB = 149.5 Hz,
4F, SF4) ; 13C NMR (100 MHz, CDCl3, ppm) d 154.1
(quintet, J = 16.9 Hz), 140.5, 132.5, 128.6, 126.6 (quin-
tet, J = 4.6 Hz), 123.9 (quintet, J = 4.6 Hz), 54.4, 43.1,
41.4, 19.8, 15.1 Anal. Calcd for C11H16F5NS: C, 45.67;
H, 5.57. Found: C, 45.52; H, 5.86.
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Acknowledgments
33. True, J. E.; Thomas, D.; Winter, R. W.; Gard, G. L. Inorg.
Chem. 2003, 42, 4437.
The support of this work by Air Products and
Chemicals is gratefully acknowledged as well as the
invaluable assistance of the NIMH Psychoactive Drug
Screening Program (N01-MH80002) administered by
Bryan L. Roth of University of North Carolina Chapel
Hill.
34. Saethre, L. J.; Berrah, N.; Bozek, J. D.; Boerve, K. J.;
Carroll, T. X.; Kukk, E.; Gard, G. L.; Winter, R.;
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