Synthesis of Aryl-Substituted Piperidines
J . Org. Chem., Vol. 64, No. 18, 1999 6705
2.31 (m, 2H), 2.52-2.68 (broad s, 8 H), 7.18-7.25 (m, 4 H),
7.34-7.37 (m, 6H); 13C NMR (75 MHz, CHCl3) δ, ppm 12.0,
20.2, 36.2, 44.7, 50.6, 60.1, 125.6, 127.2, 128.2, 128.3; EI MS
279 (M+); HRMS calcd for C20H25N 279.1987, found 279.1989.
4,4-Dip h en yl-N-ben zylp ip er id in e (10): 1H NMR (300
MHz, CHCl3) δ, ppm 2.42-2.56 (m, 8 H), 3.40 (s, 2H), 7.10-
7.16 (m, 4 H), 7.23-7.34 (m, 11H); 13C NMR (75 MHz, CHCl3)
δ, ppm 36.2, 44.7, 50.7, 63.3, 125.6, 127.0, 127.2, 128.2, 128.3,
3,3-Bis(4-ch lor op h en yl)-1-a za bicyclo[2.2.2]octa n e (15):
1H NMR (300 MHz, CHCl3) δ, ppm 1.56 (m, 2H), 1.65 (m, 2H),
2.78 (m, 4H), 2.87 (m, 1H), 3.84 (s, 2H), 7.04-7.09 (m, 2H),
7.19-7.30 (m, 6H); 13C NMR (75 MHz, CHCl3) δ, ppm 23.2,
28.7, 47.0, 58.6, 125.4, 126.6, 128.3, 148.3; EI MS 331 (M+);
HRMS calcd for C19H19Cl2N 331.0895, found 331.0896.
N-P r op yl-4,4-b is(p en t a d eu t er iop h en yl)-3,3,5,5-t et r a -
d eu ter iop ip er id in e (19): 1H NMR (300 MHz, CHCl3) δ, ppm
0.86 (t, J ) 7.2 Hz, 3H), 1.50 (m, 2H), 2.22 (m, 2H) 2.50 (s,
4H); 13C NMR (75 MHz, CHCl3) δ, ppm 12.0, 20.2, 35.4, 50.5,
50.5, 60.9, 125.4, 127.1, 127.8, 128.1; EI MS 293 (M+); HRMS
calcd for C20H11D14N 293.2866, found 293.2855.
3,3-Bis(p en t a d eu t er iop h en yl)-2,2-d id eu t er o-1-a za b i-
cyclo[2.2.2]octa n e (20): 1H NMR (300 MHz, CHCl3) δ, ppm
1.56 (m, 2H), 1.65 (m, 2H), 1.97 (m, 2H), 2.43 (m, 1H), 2.79
(m, 2H); 13C NMR (75 MHz, CHCl3) δ, ppm 23.4, 25.6, 28.7,
39.6, 46.9, 125.0, 126.5, 127.7, 128.0; EI MS 275 (M+); HRMS
calcd for C19H9D12N 275.2427, found 275.2418.
128.3, 129.2, 138.7; EI MS 327 (M+); HRMS calcd for C24H25
327.1987, found 327.1985.
N
3,3-Diph en yl-N-eth ylpiper idin e (11): 1H NMR (300 MHz,
CHCl3) δ, ppm 1.23 (t, J ) 7.5 Hz, 3H), 1.62 (m, 2H), 2.35 (m,
2H), 2.47-2.58 (m, 4H), 2.94 (s, 2H), 7.16-7.22 (m, 2H), 7.28-
7.38 (m, 4H); 13C NMR (75 MHz, CHCl3) δ, ppm 11.8, 22.4,
35.5, 46.3, 52.6, 54.3, 62.5, 125.5, 127.6, 127.9; EI MS 265 (M+);
HRMS calcd for C19H23N 265.1831, found 265.1818.
3,3-Dip h en yl-N-ben zylp ip er id in e (12): 1H NMR (300
MHz, CHCl3) δ, ppm 1.68 (m, 2H), 2.40 (m, 2H), 2.58 (m, 2H),
3.00 (m, 2H), 3.64 (s, 2H), 7.20-7.28 (m, 2H), 7.33-7.38 (m,
8H), 7.43-7.47 (m, 5H); 13C NMR (75 MHz, CHCl3) δ, ppm
22.3, 35.4, 46.6, 54.2, 63.2, 63.5, 125.6, 127.0, 127.8, 127.9,
N-(2,2-Dip h en yleth yl)p ip er id in e (24): 1H NMR (300
MHz, CHCl3) δ, ppm 1.36 (m, 2H), 1.48 (m, 4H), 2.39 (m, 4H),
2.95 (d, J ) 7.2 Hz, 2H), 4.23 (t, J ) 7.2 Hz, 1H), 7.13-7.26
(m, 10H); 13C NMR (75 MHz, CHCl3) δ, ppm 24.4, 25.9, 48.8,
54.9, 64.5, 126.1, 128.2, 128.3, 144.3; EI MS 98 (M - 167);
HRMS(DCI/NH3) calcd for C19H25N (MH+) 266.1909, found
266.1897.
128.1, 129.3, 138.6; EI MS 327 (M+); HRMS calcd for C24H25
327.1987, found 327.1987.
N
3,3-Dip h en yl-N-m eth yl-8-a za bicyclo[3.2.1]octa n e (13):
1H NMR (300 MHz, CHCl3) δ, ppm 1.48 (m, 2H), 1.82 (m, 2H),
2.42 (s, 3H), 2.61 (m, 2H), 3.07 (m, 2H), 3.39 (m, 2H), 7.40-
7.14 (m, 2H), 7.21-7.26 (m, 4H), 7.30-7.41 (m, 2H), 7.66-
7.69 (m, 2H); 13C NMR (75 MHz, CHCl3) δ, ppm 24.2, 39.0,
39.3, 42.2, 61.0, 124.6, 125.0, 125.4, 125.5, 126.7, 127.8, 127.9,
128.2; EI MS 277 (M+); HRMS calcd for C20H23N 277.1831,
found 277.1844.
Ack n ow led gm en t. Financial support from the Na-
tional Institutes of Health (SO6GM53933-0251) is grate-
fully acknowledged. The assistance of Mr. Siufu Lau is
appreciated. We also thank the reviewers for their
suggestions and comments.
3,3-Dip h en yl-1-a za bicyclo[2.2.2]octa n e (14): 1H NMR
(300 MHz, CHCl3) δ, ppm 1.66 (m, 4H), 2.86 (m, 4H), 2.95 (m,
1H), 3.93 (s, 2H), 7.06-7.16 (m, 2H), 7.18-7.30 (m, 8 H); 13C
NMR (75 MHz, CHCl3) δ, ppm 22.5, 28.5, 45.9, 46.7, 57.9,
125.7, 126.4, 128.5, 147.5; EI MS 263 (M+); HRMS calcd for
Su p p or t in g In for m a t ion Ava ila b le: 1H and 13C NMR
spectra for compounds 8-15, 20, 21, and 24. This material is
C
19H21N 263.1674, found 263.1675.
J O990454I