CH2), 2.91 (br m, 1H, CH2), 3.47 (br m, 2H, CH2’s), 4.35 (s, 2H,
CH2), 7.44 (m, 2H, aromatic Hs), 7.63 (m, 2H, aromatic Hs),
11.27 (br, 1H, HCl).
3-Ethyl-1-(3-phenylprop-2-ynyl)piperidine hydrochloride (24)
1H NMR (DMSO-d6) δ 0.86 (t, 3H, CH3), 1.08 (m, 1H, CH),
1.27 (m, 2H, CH2), 1.80 (br m, 4H, CH2), 2.65 (br t, 1H, CH2),
2.91 (br m, 1H, CH2), 3.44 (br m, 2H, CH2), 4.27 (s, 2H, CH2),
7.45 (m, 3H, aromatic Hs), 7.54 (m, 2H, aromatic H), 11.50 (br,
1H, HCl).
1-[3-(2,3-Dichlorophenyl)prop-2-ynyl]-3-methylpiperidine
hydrochloride (13)
1H NMR (DMSO-d6) δ 0.90 (d, 3H, CH3), 1.04 (m, 1H, CH),
1.82 (br m, 3H, CH2’s), 1.99 (br m, 1H, CH2), 2.66 (br t, 1H,
CH2), 2.91 (br m, 1H, CH2), 3.47 (br m, 2H, CH2’s), 4.38 (s, 2H,
CH2), 7.42 (t, 1H, aromatic H), 7.71 (m, 2H, aromatic Hs),
11.20 (br, 1H, HCl).
2-Ethyl-1-(3-phenylprop-2-ynyl)piperidine hydrochloride (25)
1H NMR (DMSO-d6) δ 0.92 (t, 3H, CH3), 1.71 (m, 8H, CH2’s),
3.16 (m, 2H, CH2), 3.50 (br m, 1H, CH), 4.31 (m, 2H, CH2),
7.43 (m, 3H, aromatic Hs), 7.54 (m, 2H, aromatic H).
1-[3-(2,4-Dichlorophenyl)prop-2-ynyl]-3-methylpiperidine
hydrochloride (14)
2-Propyl-1-(3-phenylprop-2-ynyl)piperidine hydrochloride (26)
1H NMR (DMSO-d6) δ 0.89 (t, 3H, CH3), 1.63 (m, 10H, CH2’s),
3.18 (m, 2H, CH2), 3.50 (br m, 1H, CH), 4.35 (m, 2H, CH2),
7.44 (m, 3H, aromatic Hs), 7.53 (m, 2H, aromatic H).
1H NMR (DMSO-d6) δ 0.91 (d, 3H, CH3), 1.05 (m, 1H, CH),
1.80 (br m, 3H, CH2’s), 1.99 (br m, 1H, CH2), 2.62 (br t, 1H,
CH2), 2.87 (br m, 1H, CH2), 3.46 (br m, 2H, CH2’s), 4.28 (s, 2H,
CH2), 7.53 (dd, 1H, aromatic H), 7.70 (d, 1H, aromatic H), 7.89
(d, 1H, aromatic H), 11.16 (br, 1H, HCl).
2-Methyl-1-(3-phenylprop-2-ynyl)pyrrolidine hydrochloride (27)
1H NMR (DMSO-d6) δ 1.41 (d, 3H, CH3), 1.67 (m, 1H, CH),
1.97 (m, 2H, CH2), 2.21 (m, 1H, CH), 3.26 (m, 1H, CH), 3.56
(m, 2H, CH2), 4.36 (br q, 2H, CH2), 7.44 (m, 3H, aromatic Hs),
7.53 (m, 2H, aromatic H).
1-[3-(2,5-Dichlorophenyl)prop-2-ynyl]-3-methylpiperidine
hydrochloride (15)
1H NMR (DMSO-d6) δ 0.91 (d, 3H, CH3), 1.06 (m, 1H, CH),
1.82 (br m, 3H, CH2’s), 1.95 (br m, 1H, CH2), 2.65 (br t, 1H,
CH2), 2.91 (br m, 1H, CH2), 3.46 (br m, 2H, CH2’s), 4.37 (s, 2H,
CH2), 7.59 (m, 2H, aromatic Hs), 7.84 (d, 1H, aromatic H),
11.16 (br, 1H, HCl).
(2R*,3R*)-2,3-Dimethyl-1-(3-phenylprop-2-ynyl)piperidine
hydrochloride (28) [cis]
1H NMR (DMSO-d6) δ 0.89 (d, 2H, CH3), 0.99 (d, 1H, CH3),
1.13 (d, 2H, CH3), 1.29 (d, 1H, CH3), 1.43 (m, 1H, CH2), 1.76
(m, 2H, CH2), 2.20 (br, 1H, CH), 3.15 (m, 3H, CH2), 3.63 (m,
1H, CH), 4.25 (m, 1.5H, CH2), 4.37 (d, 0.5H, CH2), 7.44 (m,
3H, aromatic Hs), 7.53 (m, 2H, aromatic Hs).
1-[3-(2,6-Dichlorophenyl)prop-2-ynyl]-3-methylpiperidine
hydrochloride (16)
1H NMR (DMSO-d6) δ 0.91 (d, 3H, CH3), 1.01 (m, 1H, CH),
1.80 (br m, 3H, CH2’s), 1.98 (br m, 1H, CH2), 2.66 (br t, 1H,
CH2), 2.93 (br m, 1H, CH2), 3.48 (br m, 2H, CH2’s), 4.45 (s, 2H,
CH2), 7.48 (dd, 1H, aromatic H), 7.60 (s, 1H, aromatic H), 7.64
(d, 1H, aromatic H), 11.22 (br, 1H, HCl).
(2R*,3S*)-2,3-Dimethyl-1-(3-phenylprop-2-ynyl)piperidine
hydrochloride (29) [trans]
1H NMR (DMSO-d6) δ 0.95 (d, 3H, CH3), 1.25 (m, 1H, CH),
1.36 (d, 3H, CH3), 1.81 (m, 4H, CH2), 3.09 (m, 2H, CH2), 3.52
(br d, 1H, CH), 4.37 (br s, 2H, CH2), 7.43 (m, 3H, aromatic Hs),
7.55 (m, 2H, aromatic Hs), 11.16 (br, 1H, HCl).
1-[3-(4-Chloro-3-trifluoromethylphenyl)prop-2-ynyl]-3-methyl-
piperidine hydrochloride (17)
1H NMR (DMSO-d6) δ 0.91 (d, 3H, CH3), 1.08 (m, 1H, CH),
1.82 (br m, 3H, CH2’s), 1.96 (br m, 1H, CH2), 2.63 (br t, 1H,
CH2), 2.89 (br m, 1H, CH2), 3.46 (br m, 2H, CH2’s), 4.30 (s, 2H,
CH2), 7.84 (m, 2H, aromatic Hs), 8.01 (s, 1H, aromatic H).
(2R*,5S*)-2,5-Dimethyl-1-(3-phenylprop-2-ynyl)piperidine
hydrochloride (30) [cis]
1H NMR (DMSO-d6) δ 0.91 (d, 2H, CH3), 1.06 (d, 1H, CH3),
1.26 (d, 2H, CH3), 1.39 (d, 1H, CH3), 1.62 (m, 2H, CH2), 2.07
(m, 2H, CH2), 2.72 (br q, 1H, CH), 3.18 (m, 1.5H, CH2), 3.47
(m, 0.5H, CH2), 3.85 (br s, 1H, CH), 4.21 (m, 1.5H, CH2), 4.42
(d, 0.5H, CH2), 7.43 (m, 3H, aromatic Hs), 7.52 (m, 2H,
aromatic Hs).
1-[3-(3,4-Dichlorophenyl)prop-2-ynyl]-3-methylpiperidine
hydrochloride (18)
1H NMR (DMSO-d6) δ 0.90 (d, 3H, CH3), 1.06 (m, 1H, CH),
1.82 (br m, 3H, CH2’s), 1.95 (br m, 1H, CH2), 2.62 (br t, 1H,
CH2), 2.86 (br m, 1H, CH2), 3.46 (br m, 2H, CH2’s), 4.27 (s, 2H,
CH2), 7.53 (dd, 1H, aromatic H), 7.70 (d, 1H, aromatic H), 7.88
(d, 1H, aromatic H).
(2R*,5R*)-2,5-Dimethyl-1-(3-phenylprop-2-ynyl)piperidine
hydrochloride (31) [trans]
1H NMR (DMSO-d6) δ 0.90 (d, 3H, CH3), 1.23 (m, 1H, CH),
1.34 (d, 3H, CH3), 1.79 (m, 3H, CH2), 2.05 (m, 1H, CH), 2.74
(br q, 1H, CH), 3.22 (br, 1H, CH), 3.44 (m, 1H, CH2), 4.34 (br s,
2H, CH2), 7.44 (m, 3H, aromatic Hs), 7.55 (m, 2H, aromatic
Hs).
1-[3-(3-Chloro-5-methoxy)prop-2-ynyl]-3-methylpiperidine
hydrochloride (20)
1H NMR (DMSO-d6) δ 0.91 (d, 3H, CH3), 1.05 (m, 1H, CH),
1.82 (br m, 3H, CH2’s), 1.99 (br m, 1H, CH2), 2.61 (br t, 1H,
CH2), 2.86 (br m, 1H, CH2), 3.47 (br m, 2H, CH2’s), 3.79 (s, 3H,
OCH3), 4.26 (s, 2H, CH2), 7.07 (m, 1H, aromatic H), 7.14 (m,
1H, aromatic H), 7.21 (m, 1H, aromatic H), 11.21 (br, 1H,
HCl).
(2Ri*,6S*)-2,6-Dimethyl-1-(3-phenylprop-2-ynyl)piperidine
hydrochloride (32) [cis]
1H NMR (DMSO-d6) δ 1.38 (d, 6H, CH3), 1.67 (m, 6H, CH2’s),
3.37 (m, 2H, CH2), 4.38 (s, 2H, CH2), 7.43 (m, 3H, aromatic H),
7.56 (m, 2H, aromatic H), 11.04 (br, 1H, HCl).
1-[3-(3,5-Difluorophenyl)prop-2-ynyl]-3-methylpiperidine
hydrochloride (21)
(3R*,5S*)-3,5-Dimethyl-1-(3-phenylprop-2-ynyl)piperidine
hydrochloride (33) [cis]
1H NMR (DMSO-d6) δ 0.91 (d, 6H, CH3’s), 1.75 (br d, 1H,
1H NMR (DMSO-d6) δ 0.91 (d, 3H, CH3), 1.05 (m, 1H, CH),
1.76 (br m, 3H, CH2’s), 1.97 (br m, 1H, CH2), 2.62 (br t, 1H,
CH2), 2.89 (br m, 1H, CH2), 3.53 (br m, 2H, CH2), 4.29 (s, 2H,
CH2), 7.39 (m, 3H, aromatic Hs), 11.11 (br, 1H, HCl).
CH), 2.02 (br, 2H, CH2), 2.55 (br, 2H, CH2), 3.42 (m, 3H, CH2),
O r g . B i o m o l . C h e m . , 2 0 0 3 , 1, 4 9 8 – 5 0 6
503