20
S. Busi et al. / Journal of Molecular Structure 787 (2006) 18–30
reaction time 72 h. The yield (white powder) was 2.30 g (23%).
1
Elemental analysis: calculated for C H NCl: C, 74.59; H,
18 24
H NMR (CDCl , 500 MHz, ppm): 2.50 (6H, s, CH ), 3.14
3
8.35; N, 4.83. Found: C, 73.16; H, 8.28; N, 4.59.
3
(
6H, s, CH ), 5.26 (4H, s, Ph–CH ), 7.22 (2H, t, Ar–H), 7.25
3 2
1
3
( C
NMR (CDCl , 126 MHz, ppm): 20.64 (2C, CH ), 48.29 (2C,
2H, d, Ar–H), 7.33 (2H, td, Ar–H), 7.69 (2H, dd, Ar–H).
2
.1.7. Dimethyldi(3-phenylpropyl)ammonium chloride (6)
Method B. Reagents: 3-phenylpropyl chloride (9.30 ml,
2.91 mmol), sodium carbonate (6.67 g, 62.91 mmol) and
3
3
CH ), 65.20 (2C, Ph–CH ), 126.08 (2C, Ar–C), 126.46 (2C,
3
2
6
Ar–C), 130.71 (2C, Ar–C), 131.83 (2C, Ar–C), 135.15 (2C,
Ar–C), 140.12 (2C, Ar–C). ESI-TOF MS: m/z calculated for
dimethyl formamide (30 ml). Reaction temperature 100 8C
and reaction time 72 h. The yield (brown gel) was 1.4 g (14%)
C
C H NCl [MKCl] : 254.19; found: 254.12 [MKCl] .
C
1
8
24
1
.
CH CH CH –Ph), 2.67 (4H, t, N–CH CH CH –Ph), 3.36
H NMR (CDCl , 500 MHz, ppm): 1.86–1.93 (4H, m, N–
3
Elemental Analysis: Calculated for C H NCl: C, 74.59; H,
1
8 24
2
2
2
2
2
2
8
.35; N, 4.83. Found: C, 73.74; H, 8.34; N, 4.54.
(6H, s, N–CH ), 3.47–3.50 (4H, m, N–CH CH CH –Ph),
3 2 2 2
7
7
.11–7.14 (4H, m, Ar–H(2,6)), 7.18–7.21 (2H, m, Ar–H(4)),
13
.25–7.29 (4H, m, Ar–H(3,5)). C NMR (CDCl , 126 MHz,
2
.1.4. Dimethyldi(3-methylbenzyl)ammonium chloride (3)
Method A. Reagents: 3-methylbenzyl chloride (9.12 ml,
9.00 mmol), sodium carbonate (7.31 g, 69.00 mmol) and
3
ppm): 24.30 (2C, N–CH CH CH –Ph), 31.98 (2C, N–CH
2
2
2
2-
2-
6
CH CH –Ph), 51.45 (2C, N–CH ), 62.73 (2C, N–CH CH
2
2
3
2
dimethyl formamide (50 ml). Reaction temperature 75 8C and
reaction time 72 h. The yield (white powder) was 3.5 g (35%).
CH –Ph), 126.76 (2C, Ar–C(4)), 128.32 (4C, Ar–C(2,6)),
2
128.79 (4C, Ar–C(3,5)), 139.25 (2C, Ar–C(1)). ESI-TOF MS:
m/z calculated for C H NCl [MKCl] : 282.22; found:
2
C H NCl: C, 75.56; H, 8.88; N, 4.41. Found: C, 73.77; H,
1
H NMR (CDCl , 500 MHz, ppm): 2.23 (6H, s, CH ), 3.11
3
C
3
2
0 28
(
6H, s, CH ), 5.08 (4H, s, Ph–CH ), 7.17 (2H, d, Ar–H), 7.20
3
C
82.08 [MKCl] . Elemental analysis: calculated for
2
1
3
(
2H, t, Ar–H), 7.39 (2H, s, Ar–H(2)), 7.43 (2H, d, Ar–H).
C
NMR (CDCl , 126 MHz, ppm): 21.10 (2C, CH ), 48.08 (2C,
2
0 28
3
3
9.18; N, 4.52.
CH ), 67.58 (2C, Ph–CH ), 127.50 (2C, Ar–C(1)), 128.78 (2C,
3
2
Ar–C), 130.47 (2C, Ar–C), 131.15 (2C, Ar–C), 133.72 (2C,
Ar–C(2)), 138.80 (2C, Ar–C). ESI-TOF MS: m/z calculated for
2
.1.8. Dibenzyldiethylammonium chloride (7)
C
C H NCl [MKCl] : 254.19; found: 254.07 [MKCl] .
C
Method A. Reagents: benzyl chloride (7.94 ml,
69.00 mmol), sodium carbonate (7.31 g, 69.00 mmol) and
1
8 24
Elemental analysis: calculated for C H NCl: C, 74.59; H,
1
8 24
8
.35; N, 4.83. Found: C, 74.26; H, 8.36; N, 4.60.
diethyl formamide (50 ml). Reaction temperature 60 8C and
reaction time 72 h. The yield (light brown powder) was 0.40 g
1
4%). H NMR (CDCl , 500 MHz, ppm): 1.37 (6H, t, N–
(
CH CH ), 3.58 (4H, q, N–CH CH ), 5.05 (4H, s, Ph–CH ),
3
2
.1.5. Dimethyldi(4-methylbenzyl)ammonium chloride (4)
Method A. Reagents: 4-methylbenzyl chloride (9.15 ml,
9.00 mmol), sodium carbonate (7.31 g, 69.00 mmol) and
2
3
2
3
2
1
.40–7.46 (6H, m, Ar–H), 7.66–7.68 (4H, m, Ar–H). C NMR
3
7
6
(CDCl , 126 MHz, ppm): 9.50 (2C, N–CH CH ), 52.91 (2C,
N–CH CH ), 64.10 (2C, Ph–CH ), 127.94 (2C, Ar–C(1)),
3
2
3
dimethyl formamide (30 ml). Reaction temperature 80 8C and
reaction time 72 h. The yield (white powder) was 6.82 g (68%).
2
3
2
1
129.31 (4C, Ar–C), 130.60 (2C, Ar–C(4)), 133.07 (4C, Ar–C).
C
ESI-TOF MS: m/z calculated for C H NCl [MKCl] :
H NMR (CDCl , 500 MHz, ppm): 2.32 (6H, s, CH ), 3.08
3
3
1
8 24
(
6H, s, CH ), 5.05 (4H, s, Ph–CH ), 7.14 (4H, d, Ar–H), 7.51
3 2
C
1
4H, d, Ar–H). C NMR (CDCl , 126 MHz, ppm): 21.21 (2C,
3
254.19; found: 254.07 [MKCl] . Elemental analysis: calcu-
lated for C H NCl: C, 74.59; H, 8.35; N, 4.83. Found: C,
(
CH ), 47.93 (2C, CH ), 67.44 (2C, Ph–CH ), 124.54 (2C, Ar–
3
1
8 24
3
3
2
73.93; H, 8.40; N, 4.65.
C), 129.70 (4C, Ar–C), 133.25 (4C, Ar–C), 140.69 (2C, Ar–C)
C
.
ESI-TOF MS: m/z calculated for C H NCl [MKCl] :
18 24
C
54.19; found: 254.04 [MKCl] . Elemental analysis: calcu-
2
lated for C H NCl: C, 74.59; H, 8.35; N, 4.83. Found: C,
2
.1.9. Diethyldi(3-methylbenzyl)ammonium chloride (8)
Method B. Reagents: 3-methylbenzyl chloride (8.70 ml,
5.82 mmol), sodium carbonate (6.98 g, 65.82 mmol) and
1
8 24
7
4.39; H, 8.41; N, 4.59.
6
diethyl formamide (50 ml). Reaction temperature 80 8C and
reaction time 96 h. The yield (light yellow sticky powder)
2
.1.6. Dimethyldi(2-phenylethyl)ammonium chloride (5)
Method A. Reagents: 2-phenylethyl chloride (9.08 ml,
9.00 mmol), sodium carbonate (7.31 g, 69.00 mmol) and
1
was 0.60 g (6%). H NMR (CDCl
, 500 MHz, ppm): 1.35
), 3.48 (4H, q, N–
), 7.19–7.25 (4H, m, Ar–H),
2
3
6
(6H, t, N–CH
CH CH ), 4.87 (4H, s, Ph–CH
7.36–7.38 (4H, m, Ar–H). C NMR (CDCl
ppm): 9.38 (2C, N–CH CH ), 21.20 (2C, Ph–CH
(2C, N–CH CH ), 63.78 (2C, Ph–CH ), 127.67 (2C, Ar–C),
2 3 3
CH ), 2.30 (6H, s, Ph–CH
dimethyl formamide (30 ml). Reaction temperature 90 8C and
reaction time 72 h. The yield (light yellow powder) was 0.17 g
2
3
1
3
, 126 MHz,
), 52.86
3
1
2%). H NMR (CDCl , 500 MHz, ppm): 3.06–3.09 (4H, m,
(
2
3
3
3
N–CH CH –Ph), 3.50 (6H, s, N–CH ), 3.88–3.91 (4H, m, N–
2
2
3
2
2
3
CH CH –Ph), 7.23–7.26 (2H, m, Ar–H(4)), 7.28–7.32 (8H, m,
2
129.00 (2C, Ar–C), 129.93 (2C, Ar–C), 131.19 (2C, Ar–C),
133.40 (2C, Ar–C), 139.03 (2C, Ar–C). ESI-TOF MS: m/z
2
1
Ar–H). C NMR (CDCl , 126 MHz, ppm): 29.42 (2C, N–
3
3
C
CH CH –Ph), 51.34 (2C, N–CH ), 64.58 (2C, N–CH CH –
2
calculated for C20H28NCl [MKCl] : 282.22; found: 282.08
2
3
2
2
C
Ph), 127.56 (2C, Ar–C(4)), 129.02 (4C, Ar–C), 129.15 (4C,
Ar–C), 134.72 (2C, Ar–C(1)). ESI-TOF MS: m/z calculated for
[MKCl] . Elemental Analysis: Calculated for C20H28NCl:
C, 75.56; H, 8.88; N, 4.41. Found: C, 69.58; H, 8.52; N,
4.34.
C C
C H NCl [MKCl] : 254.19; found: 254.07 [MKCl] .
1
8 24