564
Table X. 1H-NMR spectra of cyclohexylamines 2*.
Compound
M.p. (°C)
1H-NMR (CDCl3, TMS) δ, ppm
2a-ax
2a-eq
2b-ax
> 250 (subl.)
200–202
> 250 (subl.)
0.89 (3H, d, 6.5 Hz); 0.7–1.0 (2H, m); 1.2–1.35 (1H, m) 1.45 (3H, s); 1.6–2.1 (6H, m); 8.3 (3H, br s)
0.91 (3H, d, 6.4 Hz); 0.85–1.0 (1H, m); 1.47 (3H, s); 1.15–1.75 (6H, m); 1.94 (2H, m); 8.3 (3H, br s)
0.88 (3H, t, 7.5 Hz); 0.7–1.0 (2H, m); 1.1–1.35 (3H, m); 1.46 (3H, s); 1.6–1.9 (4H, m); 2.0–2.15 (2H,
m); 8.35 (3H, br s)
2b-eq
2c-ax
179–181
> 250 (subl.)
0.87 (3H, t, 7 Hz); 1.45 (3H, s); 0.8–2.0 (11H, m); 8.3 (3H, br s)
0.87 (3H, t, 7.3 Hz); 0.7–1.0 (2H, m); 1.05–1.4 (5H, m); 1.45 (3H, s); 1.55–1.7 (1H, m); 1.75–1.95 (3H,
m); 2.0–2.1 (2H, m); 8.3 (3H, br s)
2c-eq
181–182
0.85 (3H, t, 7.1 Hz); 0.8–0.9 (1H, m); 1.47 (3H, s); 1.15–1.5 (7H, m); 1.6–1.8 (3H, m); 1.9–2.0 (2H,
m); 8.3 (3H, br s)
2d
2e-ax
2e-eq
230–231
> 280
237–238
0.96 (3H, s); 1.06 (3H, s); 1.15–1.40 (2H, m); 1.50 (3H, s); 1.5–1.85 (6H, m); 8.25 (3H, br s)
0.4–0.6 (1H, m); 0.90 (6H, d, 6.5 Hz); 0.8–1.1 (2H, m); 1.44 (3H, s); 1.6–2.15 (5H, m); 8.3 (3H, br s)
0.45–0.75 (1H, m); 0.90 (6H, d, 5 Hz); 1.47 (3H, s); 1.2–1.7 (6H, m); 1.94 (2H, d, 11.5); 8.3 (3H, br
s)
2f-ax
2f-eq
2g-ax
2g-eq
2h-ax
> 240
0.72 (1H, t, 12.5 Hz); 0.90 and 0.91 (total 6H, d, 6.5 Hz and s); 0.85–1.0 (1H, m); 1.16 (1H d, 14.8
Hz); 1.23 (3H, s); 1.45 (3H, s); 1.4–1.55 (1H, m); 1.85–2.0 (2H, m); 2.1 (1H, m); 8.2 (3H, br s)
0.96, 1.0 and 1.04 (total 9H, d, 6 Hz, s and s); 0.9–1.1 (1H, m); 1.37 (1H, t, 12 Hz); 1.44 (1H, d, 13
Hz); 1.61 (3H, s); 1.6–1.95 (3H, m); 2.02 (1H, d, 12 Hz) 8.25 (3H, br s)
0.67 (1H, t, 13 Hz); 0.84 (3H, s); 0.85–0.95 (m, 6H); 1.07 (1H, d, 15.5 Hz); 1.48 (3H, s); 1.5–1.8 (4H,
m); 1.9–2.1 (3H, m); 8.15 (3H, br s)
0.83 (3H, t, 7.5 Hz); 0.88 (3H, s); 0.91 (3H, d, 6.5 Hz); 0.8–0.95 (1H, m); 1.55 (3H, s); 1.15–1.80 (6H,
m); 1.9–2.0 (2H, m); 8.3 (3H, br s)
0.61 (1H, t, 13 Hz); 0.86 (3H, s); 0.89 (3H, d, 6 Hz); 0.85–1.0 (1H, m); 1.00 (3H, t, 7 Hz); 1.13 (1H,
d, 15.5 Hz); 1.51 (3H, s); 1.15–1.75 (5H, m); 1.89 (1H, m); 1.95 (1H, d, 15.5 Hz); 2.11 (1H, d, 14.5
Hz); 8.2 (3H, br s)
> 240
250–253
228–231
167–168
2h-eq
2i-ax
237–238
255–257
0.8–0.95 (10H, m); 1.54 (3H, s); 1.1–1.8 (8H, m); 1.97 (2H, d, 13 Hz); 8.3 (3H, br s)
0.72 (1H, t, 13 Hz); 0.91 (3H, t, 7.5 Hz); 0.92 (3H, s); 0.8–0.95 (1H, m); 1.23 (3H, s); 1.1–1.3 (3H,
m); 1.46 (3H, s); 1.51 (1H, d, 13 Hz); 1.85–2.0 (2H, m); 2.03 (1H, d, 15 Hz); 8.3 (3H, br s)
0.88 (3H, t, 7.5 Hz); 0.8–0.95 (1H, m); 0.96 (3H, s,); 0.98 (3H, s); 1.2–1.35 (3H, m); 1.56 (3H, s);
1.4–1.56 (3H, m); 1.83 (1H, d, 13 Hz); 2.01 (1H, d, 12 Hz); 8.3 (3H, br s)
0.72 (1H, t, 13 Hz); 0.89 (3H, t, 7 Hz); 0.92 (3H, s); 0.85–0.9 (1H, m); 1.23 (3H, s); 1.45 (3H, s);
1.0–2.1 (9H, m); 8.2 (3H, br s)
2i-eq
2j-ax
2j-eq
216–218
218–221
200–203
0.86 (3H, t, 7 Hz); 0.8–0.95 (1H, m); 0.95 (3H, s); 0.98 (3H, s); 1.55 (3H, s); 1.1–1.7 (8H, m); 1.83
(1H, d, 13 Hz); 1.99 (1H, d, 12 Hz); 8.3 (3H, br s)
2k
2l
235–237
215–218
1.02 (6H, s) and 1.07 (6H, s); 1.26 (2H, br s); 1.62 (3H, s); 1.71 (4H, br s)
1.03 (3H, s) 1.06 (3H, s); 1.09 (3H, t, 7.5 Hz); 1.30 (2H, br s); 1.63 and 1.78 (total 4H, both d, 14 Hz);
1.97 (2H, q, 7 Hz); 8.15 (3H, br s)
2m
2n
2o
> 280
0.93 (3H, t, 7 Hz); 1.01 (6H, s); 1.04 (6H, s); 1.29 (2H, br s); 1.35–2.0 (4H, m); 1.70 (4H, m); 8.2 (3H,
br s)
0.75–0.85 (6H, m); 1.04 (3H, s); 1.05 (3H, s); 1.19 (1H, d, 14 Hz); 1.25–1.50 (5H, m); 1.60 (3H, s);
1.67 and 1.75 (total 4H, both d, 14 Hz); 8.25 (3H, br s)
0.83–0.89 (6H, m); 1.03 (3H, s); 1.05 (3H, s); 1.15–1.45 (10H, m); 1.57 (2H, d, 14.5 Hz); 1.61 (3H,
s); 1.77 (2H, d, 14 Hz); 8.2 (3H, br s)
99–102
167–169
* 1,trans-3-Dimethylcyclohexylamine hydrochloride 2a-ax: 13C-NMR (CDCl3, 50 MHz) δ: 21.75 (C-5); 23.02 (3-CH3); 27.99 (C-3); 28.67
(1-CH3); 34.72 (C-4); 36.63 (C-6); 45.50 (C-2); 56.20 (C-1); 1,cis-3- dimethylcyclohexylamine hydrochloride semihydrate 2a-eq: 13C-NMR
(CDCl3, 50 MHz) δ: 22.9–23.05 (C-5, 3-CH3, 1-CH3); 29.71 (C-3); 34.68 (C-4); 36.87 (C-6); 45.45 (C-2); 56.81 (C-1); 1-methyl,
trans-3-ethylcyclohexylamine hydrochloride 2b-ax; 1-methyl,cis-3-ethylcyclohexylamine hydrochloride 2b-eq; 1-methyl,trans-3-
propylcyclohexylamine hydrochloride 2c-ax; 1-methyl,cis-3-propylcyclohexylamine hydrochloride 2c-eq; 1,3,3-trimethylcyclohexylamine
hydrochloride 2d; 1,trans-3, trans-5-trimethylcyclohexylamine hydrochloride 2e-ax; 1,cis-3, cis-5-trimethylcyclohexylamine hydrochloride
hydrate 2e-eq; 1,3,3,trans-5-tetramethylcyclohexylamine hydrochloride 2f-ax; 1,3,3,cis-5-tetramethylcyclohexylamine hydrochloride semi-
hydrate 2f-eq; cis-3-ethyl-1,trans-3,trans-5-trimethylcyclohexylamine hydrochloride 2g-ax; trans-3-ethyl-1,cis-3,cis-5-trimethyl-
cyclohexylamine hydrochloride 2g-eq; cis-3-propyl-1,trans-3,trans-5-trimethylcyclohexylamine hydrochloride 2h-ax; trans-3-propyl-1,cis-
3,cis-5-trimethylcyclohexylamine hydrochloride 2h-eq; 1,3,3-trimethyl-trans-5-ethylcyclohexylamine hydrochloride 2i-ax; 1,3,3-trimethyl-
cis-5-ethylcyclohexylamine hydrochloride semihydrate 2i-eq; 1,3,3-trimethyl-trans-5-propylcyclohexylamine hydrochloride 2j-ax; 1,3,3-
trimethyl-cis-5-propylcyclohexylamine hydrochloride 2j-eq; 1,3,3,5,5-pentamethylcyclohexylamine hydrochloride 2k; 1-ethyl-3,3,5,5-
tetramethylcyclohexylamine hydrochloride hydrate 2l; 1-propyl-3,3,5,5-tetramethylcyclohexylamine 2m; 3,3-diethyl-1,5,5-
trimethylcyclohexylamine hydrate 2n; 3,3-Dipropyl-1,5,5-trimethylcyclohexylamine 2o.