530
A. Pau et al. / Il Farmaco 54 (1999) 524–532
5
.1.6.4. N-[4-(tert-Butyl)cyclohexyl]-4-bromobenzamide
5.1.6.8. N-[4-(tert-Butyl)cyclohexyl]-4-nitrobenzamide
(4h). Formula (C H N O ), M 304.39, m.p. 180°C,
(
4d). Formula (C H NOBr), M 338.29, m.p. 200–
1
7
24
w
17 24
2
3
w
1
1
2
1
2
2
01°C, yield 56%. H (CDCl ): 0.88 (s, 9H, 4-C(CH ) ),
yield 97%. H (CDCl ): 0.82 (s, 9H, 4-C(CH ) ), 0.98
3
3 3
3 3 3
.00 (m, 1H, H-4), 1.18 (m, 4H, H-2 and H-6), 1.84 (bd,
(m, 1H, H-4), 1.12 (m, 4H, H-2 and H-6), 1.84 (bd, 2H,
H, J=7.4, H -3 and H -5), 2.14 (bd, 2H, J=7.4,
J=8.0, 2H, H -3 and H -5), 2.16 (bd, 2H, J=8.0,
eq
eq
eq
eq
H, H -3 and H -5), 3.84 (m, 1H, H-1), 6.02 (d, 1H,
2H, H -3 and H -5), 3.86 (m, 1H, H-1), 6.14 (d, 1H,
ax
ax
ax ax
J=6.8, NH), 7.58 (d, 2H, J=8.5 H-3% and H-5%), 7.64
J=6.8, NH), 7.90 (d, 2H, J=8.5 H-3% and H-5%), 8.24
13
13
(
d, 2H, J=8.5, H-2% and H-6%). C (CDCl ): 26.13 (2C,
(d, 2H, J=8.5, H-2% and H-6%). C (CDCl ): 26.10 (2C,
3
3
C-3 and C-5), 27.56 (3C, 4-C(CH ) ), 32.37 (1C, 4-
C-3 and C-5), 27.55 (3C, 4-C(CH ) ), 32.38 (1C, 4-
3
3
3 3
C(CH ) ), 33.62 (2C, C-2 and C-6), 47.33 (1C, C-4),
C(CH ) ), 33.53 (2C, C-2 and C-6), 47.28 (1C, C-4),
3
3
3 3
4
9.40 (1C, C-1), 125.82 (1C, C-4%), 128.52 (2C, C-3% and
49.79 (1C, C-1), 123.74 (2C, C-3% and C-5%), 128.10 (2C,
C-2% and C-6%), 140.63 (1C, C-1%), 149.42 (1C, C-4%),
164.74 (1C, CO).
C-5%), 131.67 (2C, C-2% and C-6%), 133.88 (1C, C-1%),
1
5
65.76 (1C, CO).
5.1.6.9. N-[4-(Ethyl)cyclohexyl]-3,4,5-trimetoxybenza-
.1.6.5. N-[4-(tert-Butyl)cyclohexyl]-2,4-dichlorobenza-
mide (5a). Formula (C H NO ), M 321.42, m.p.
1
8
27
4
w
mide (4e). Formula (C H NOCl ), M 328.28, m.p.
1
1
7
23
2
w
2
07–208°C, yield 94%. H (CDCl ): 0.88 (t, 3H, J=7.0,
3
1
179–180°C, yield 73%. H (CDCl ): 0.89 (s, 9H, 4-
3
4
-CH -CH ), 1.18 (m, 7H, H-4, H-2, H-6 and 4-CH -
2
3
2
C(CH ) ), 1.02 (m, 1H, H-4), 1.19 (m, 4H, H-2 and
H-6), 1.85 (bd, 2H, J=8.5, 2H, H -3 and H -5), 2.17
3
3
CH ), 1.82 (bd, 2H, J=8.0, H -3 and H -5), 2.08 (bd,
3
eq
eq
eq
eq
2
4
1
H, J=8.0, H -3 and H -5), 3.86 (m, 4H, H-1 and
ax ax
(
bd, 2H, J=8.5, 2H, H -3 and H -5), 3.86 (m, 1H,
ax ax
%-OCH ), 3.92 (s, 6H, 3%-OCH and 5%-OCH ), 5.94 (d,
3
3
3
H-1), 6.00 (d, 1H, J=6.8, NH), 7.32 (d, 1H, J=8.5
H-5%), 7.42 (s, 1H, H-3%), 7.61 (d, 1H, J=8.5, H-6%).
13
H, J=6.8, NH), 6.98 (s, 2H, H-2% and H-6%).
C
13
C
(
CDCl ): 11.61 (1C, 4-CH -CH ), 29.48 (1C, 4-CH -
3 2 3 2
(
CDCl ): 26.07 (2C, C-3 and C-5), 27.50 (3C, 4-
3
CH ), 31.44 (2C, C-3 and C-5), 33.26 (2C, C-2 and
3
C(CH ) ), 32.32 (4-C(CH ) ), 33.44 (2C, C-2 and C-6),
3
3
3 3
C-6), 38.69 (1C, C-4), 49.45 (1C, C-1), 56.35 (2C,
47.33 (1C, C-4), 49.71 (1C, C-1), 127.41, 129.88 and
131.14 (1C, C-3%, C-5% and C-6%), 131.24 (1C, C-1%),
133.93 and 136.43 (2C, C-2% and C-4%), 164.79 (1C, CO).
3
%-OCH and 5%-OCH ), 60.90 (1C, 4%-OCH ), 104.25
3 3 3
(
2C, C-2% and C-6%), 130.65 (1C, C-1%), 153.16 (3C, C-3%,
C-4% and C-5%), 166.46 (1C, CO).
5
.1.6.10. N - [4 - (Ethyl)cyclohexyl] -4-chlorobenzamide
5
.1.6.6. N-[4-(tert-Butyl)cyclohexyl]benzamide (4f). For-
(
5b). Formula (C H NOCl), M 265.79, m.p. 168–
15
20
w
mula (C H NO), M 259.39, m.p. 172–173°C, yield
9
1
7
25
w
1
1
170°C, yield 75%. H (CDCl ): 0.85 (t, 3H, J=7.0,
4
CH ), 1.82 (bd, 2H, J=8.0, 2H, H -3 and H -5), 2.10
3
4%. H (CDCl ): 0.88 (s, 9H, 4-C(CH ) ), 0.98 (m, 1H,
3 3 3
-CH -CH ), 1.16 (m, 7H, H-4, H-2, H-6 and 4-CH -
2 3 2
H-4), 1.18 (m, 4H, H-2 and H-6), 1.82 (bd, 2H, J=7.5,
H, H -3 and H -5), 2.12 (bd, 2H, J=7.5, 2H, H -3
3
eq
eq
2
eq
eq
ax
(
bd, 2H, J=8.0, 2H, H -3 and H -5), 3.86 (m, 1H,
ax ax
and H -5), 3.86 (m, 1H, H-1), 6.06 (d, 1H, J=6.8,
NH), 7.42 (t, 2H, J=8.5, H-3% and H-5%), 7.48 (t, 1H,
J=8.5, H-4%), 7.78 (d, 2H, J=8.5, H-2% and H-6%).
ax
H-1), 5.90 (d, 1H, J=6.8, NH), 7.40 (d, 2H, J=8.5,
H-3% and H-5%), 7.70 (d, 2H, J=8.5, H-2% and H-6%).
1
3
13
C
C
(
CDCl ): 11.60 (1C, 4-CH -CH ), 29.45 (1C, 4-CH -
3
2
3
2
(
CDCl ): 26.16 (2C, C-3 and C-5), 27.56 (3C, 4-
3
CH ), 31.40 (2C, C-3 and C-5), 33.23 (2C, C-2 and
C-6), 38.64 (1C, C-4), 49.43 (1C, C-1), 128.28 (2C, C-3%
and C-5%), 128.74 (2C, C-2% and C-6%), 133.40 (1C, C-1%),
3
C(CH ) ), 32.35 (1C, 4-C(CH ) ), 33.65 (2C, C-2 and
C-6), 47.35 (1C, C-4), 49.23 (1C, C-1), 126.86 (2C, C-3%
and C-5%), 128.43 (2C, C-2% and C-6%), 131.16 (1C, C-4%),
3
3
3 3
1
37.43 (1C, C-4%), 165.63 (1C, CO).
1
35.09 (1C, C-1%), 166.89 (1C, CO).
5.1.6.11. N-[4-(Ethyl)cyclohexyl]-4-fluorobenzamide
5
.1.6.7. N-[4-(tert-Butyl)cyclohexyl]-4-methylbenzamide
(5c). Formula (C H NOF), M 249.33, m.p. 190–
15
20
w
1
(
4g). Formula (C H NO), M 273.42, m.p. 178–
191°C, yield 78%. H (CDCl ): 0.87 (t, 3H, J=7.0,
1
1
8
27
w
3
1
0
2
7
79°C, yield 94%. H (CDCl ): 0.85 (s, 9H, 4-C(CH ) ),
4-CH -CH ), 1.19 (m, 7H, H-4, H-2, H-6 and 4-CH -
3
3 3
2
3
2
.96 (m, 1H, H-4), 1.16 (m, 4H, H-2 and H-6), 1.82 (bd,
CH ), 1.82 (bd, 2H, J=7.7, 2H, H -3 and H -5), 2.11
3 eq eq
H, J=7.5, 2H, H -3 and H -5), 2.12 (bd, 2H, J=
(bd, 2H, J=7.7, 2H, H -3 and H -5), 3.88 (m, 1H,
ax ax
eq
eq
.5, H -3 and H -5), 2.38 (s, 3H, 4%-CH ), 3.86 (m, 1H,
H-1), 6.01 (d, 1H, J=6.8, NH), 7.05 (t, 2H, J=8.8,
H-3% and H-5%), 7.74 (dd, 2H, J=8.8, 5.1, H-2% and
ax
ax
3
H-1), 6.03 (d, 1H, J=6.8, NH), 7.20 (d, 2H, J=8.5,
H-3% and H-5%), 7.66 (d, 2H, J=8.5, H-2% and H-6%).
13
13
C
H-6%). C (CDCl ): 11.61 (1C, 4-CH -CH ), 29.45 (1C,
3
2
3
(
CDCl ): 21.33 (1C, 4%-CH ), 26.13 (2C, C-3 and C-5),
4-CH -CH ), 31.47 (2C, C-3 and C-5), 33.28 (2C, C-2
3
3
2 3
2
7.52 (3C, 4-C(CH ) ), 32.31 (1C, 4-C(CH ) ), 33.65
and C-6), 38.70 (1C, C-4), 49.45 (1C, C-1), 115.45 (2C,
3
3
3 3
(
2C, C-2 and C-6), 47.34 (1C, C-4), 49.09 (1C, C-1),
d, JCꢀF=22.9, C-3% and C-5%), 129.17 (2C, d, JCꢀF=9.5,
1
1
26.81 (2C, C-3% and C-5%), 129.04 (2C, C-2% and C-6%),
31.95 (1C, C-1%), 141.43 (1C, C-4%), 166.61 (1C, CO).
C-2% and C-6%), 131.00 (1C, C-1%), 164.63 (1C, d, JCꢀF
251.8, C-4%), 165.71 (1C, CO).
=