), 66.86 (2C, Ph–CH ),
127.97 (2C, Ar–C(1)), 128.84 (4C, Ar–C), 130.21 (2C, Ar–
Diethyldimethylammonium bromide (1). Method A. Reagents:
ethyl bromide (6.51 ml, 87.86 mmol), potassium carbonate
126 MHz, ppm): 48.01 (2C, N–CH
3
2
(
18.21 g, 131.80 mmol) and dimethylformamide (50 ml). Reac-
C(4)), 133.08 (4C, Ar–C). ESI-TOF-MS: m/z calcd for
+
tion temperature 35 1C and reaction time 66 h. Yield (white
C
C
16
16
H
20NBr [M ꢀ Br] : 226.2; found: 226.2. Anal. calcd for
1
powder): 1.92 g (24%). H NMR (CDCl , 500 MHz, ppm):
H20NBr: C, 62.75; H, 6.58; N, 4.57; found: C, 61.65; H,
3
1
3
.29 (6H, t, J = 7.29 Hz, N–CH
.56 (4H, quartet, J = 7.30 Hz, N–CH CH ). C NMR
2
CH
3
), 3.20 (6H, s, N–CH
1
3
),
6.55; N, 4.39 (yygroscopic, results match when 0.25 water is
added).
3
2
3
(
CDCl
N–CH ), 58.78 (2C, N–CH CH ). ESI-TOF-MS: m/z calcd for
3 2 3
, 126 MHz, ppm): 8.26 (2C, N–CH CH ), 49.81 (2C,
3
2
3
Dibenzyldiethylammonium bromide (6). Method A. Reagents:
benzyl bromide (5.68 ml, 47.86 mmol), potassium carbonate
+
C
C
6
H
H
16NBr [M ꢀ Br] : 102.13; found: 102.08. Anal. calcd for
6
16NBr: C, 39.57; H, 8.86; N, 7.69; found: C, 41.00; H, 8.81;
(
9.92 g, 71.79 mmol) and diethylformamide (60 ml). Reaction
N, 6.27 (very hygroscopic and sticky even after drying; results
match when water and crystallization solvent, toluene, are
added).
temperature 50 1C and reaction time 64 h. Yield (white
powder): 3.52 g (44%). H NMR (DMSO, 500 MHz, ppm):
1
1
.35 (6H, t, J = 7.16 Hz, N–CH
.16 Hz, N–CH CH ), 4.59 (4H, s, Ph–CH
2
2
CH
3
), 3.24 (4H, quartet, J =
), 7.49–7.56 (6H, m,
7
2
3
1
3
Dimethyldipropylammonium bromide (2). Method A. Re-
agents: propyl bromide (8.64 ml, 95.17 mmol), potassium
carbonate (9.86 g, 71.38 mmol) and dimethylformamide (30
Ar–H), 7.61-7.62 (4H, m, Ar–H). C NMR (DMSO, 126
MHz, ppm): 8.39 (2C, N–CH CH ), 52.54 (2C, N–CH CH ),
61.73 (2C, Ph–CH ), 127.95 (2C, Ar–C(1)), 128.94 (4C, Ar–C),
130.16 (2C, Ar–C(4)), 132.85 (4C, Ar–C). ESI-TOF-MS: m/z
2
3
2
3
2
ml). Reaction temperature 65 1C and reaction time 72 h. Yield
1
white powder): 3.11 g (31%). H NMR (CDCl , 500 MHz,
+
(
ppm): 1.03 (6H, t, J = 7.32 Hz, N–CH
calcd for C18
calcd for C18
64.34; H, 7.28; N, 4.09.
H
24NBr [M ꢀ Br] : 254.2; found: 254.2. Anal.
3
CH
2
CH ), 1.78 (4H, m,
3
H24NBr: C, 64.67; H, 7.24; N, 4.19; found: C,
2
N–CH CH CH ), 3.39 (6H, s, N–CH ), 3.51 (4H, m, N–C
3
2
2
3
1
3
). C NMR (CDCl
H
N–CH CH CH ), 16.29 (2C, N–CH CH CH ), 51.22 (2C,
2
CH
2
CH
3
3
, 126 MHz, ppm): 10.64 (2C,
2
2
3
2
2
3
Tetraethylammonium bromide (7). Commercially available
material. Method A. Reagents: ethyl bromide (3.55 ml, 47.58
mmol), potassium carbonate (6.58g, 71.37 mmol) and diethyl-
formamide (30 ml). Yield (white powder): 1.3 g (26%). The
N–CH
3
2 2 3
), 65.48 (2C, N–CH CH CH ). ESI-TOF-MS: m/z
+
calcd for C H NBr [M ꢀ Br] : 130.16; found: 130.12. Anal.
8
20
8
calcd for C H20NBr: C, 45.72; H, 9.59; N, 6.66; found: C,
4
5.06; H, 9.72; N, 6.69.
1
13
formation of compound 7 was confirmed by H and C NMR
and by ESI TOF MS.
Dibutyldimethylammonium bromide (3). Method A. Reagents:
butyl bromide (9.02 ml, 83.96 mmol), potassium carbonate
8.70 g, 62.97 mmol) and dimethylformamide (30 ml). Reaction
temperature 80 1C and reaction time 72 h. Yield (white
Dimethyldipentylammonium iodide (8). Method C. Reagents:
pentyl iodide (8.34 ml, 63.84 mmol), potassium carbonate (8.82
g, 63.84 mmol) and dimethylformamide (30 ml). Reaction
(
1
powder): 2.42 g (24%). H NMR (CDCl
.95 (6H, t, J = 7.36 Hz, N–CH CH CH
sextet, J = 7.42 Hz, N–CH CH CH CH ), 1.67 (4H, m, N–
CH CH CH CH ), 3.35 (6H, s, N–CH ), 3.53 (4H, m, N–C
CH CH CH , 126 MHz, ppm): 13.59
2C, N–CH CH ), 19.51 (2C, N–CH CH CH CH ),
4.57 (2C, N–CH CH CH ), 51.10 (2C, N–CH ), 63.74
2C, N–CH CH CH CH ). ESI-TOF-MS: m/z calcd for
24NBr [M ꢀ Br] : 158.19; found: 158.15. Anal. calcd for
C H NBr: C, 50.42; H, 10.16; N, 5.88; found: C, 50.72; H,
3
, 500 MHz, ppm):
temperature 80 1C and reaction time 48 h. Yield (white
1
0
2
2
2
CH ), 1.41 (4H,
3
powder): 2.00 g (20%). H NMR (CDCl
3
, 500 MHz, ppm):
(CH CH ), 1.38 (8H,
), 1.72 (4H, m, N–CH
), 3.36 (6H, s, N–CH ), 3.53 (4H, m, N–C
). C NMR (CDCl , 126 MHz, ppm):
), 22.19, 22.45 and 28.11
), 51.46 (2C, N–CH ), 64.26 (2C, N–
2
2
2
3
0
.90 (6H, t, J = 6.96 Hz, N–CH
2
CH
)
2
2
2
3
2
2
2
3
3
m, N–CH CH (CH CH
2
)
2
C
2
2
2
3
1
3
H
2
2
2
3
). C NMR (CDCl
CH CH
CH
3
H
H
2
2
(CH
CH
2
)
2
CH
(CH
3
2
3
1
3
(
2
2
2
3
2
2
2
3
2
2
)
CH
3
3
2
2
2
2
3
3
1
3.74 (2C, N–CH
2
CH
CH
2
2 2 3
(CH ) CH
(
2
2
2
+
3
(
6C, N–CH (CH
2
2
)
3
3
3
10
C H
CH CH (CH ) CH ). ESI-TOF-MS: m/z calcd for C H NI
2
2
+
2 2
3
12 28
1
0
24
[M ꢀ I] : 186.22; found: 186.21. Anal. calcd for C H NI: C,
1
2
28
1
0.43; N, 5.95.
4
6.01; H, 9.01; N, 4.47; found: C, 46.01; H, 9.18; N, 4.34.
Dimethyldipentylammonium bromide (4). Method B. Re-
agents: pentyl bromide (9.32 ml, 75.12 mmol), potassium
carbonate (10.38 g, 75.12 mmol) and dimethylformamide (30
Dibenzyldimethylammonium chloride (9). Method A. Re-
agents: benzyl chloride (8.79 ml, 76.40 mmol), sodium carbo-
nate (8.10 g, 76.40 mmol) and dimethylformamide (30 ml).
Reaction temperature 80 1C and reaction time 72 h. Yield
ml). Reaction temperature 80 1C and reaction time 69 h. Yield
1
brown gel): 3.19 g (32%). H NMR (CDCl
1
(
3
, 500 MHz, ppm):
(white powder): 3.12 g (31%). H NMR (CDCl , 500 MHz,
ppm): 3.12 (6H, s, N–CH ), 5.16 (4H, s, Ph–CH ), 7.33 (4H, t,
3
0
m, N–CH
.88 (6H, t, J = 6.88 Hz, N–CH CH (CH ) CH ), 1.35 (8H,
3
2
2
2 2
3
2
1
3
2
CH
2
(CH
2
)
2
CH
3
), 1.68 (4H, m, N–CH
H (CH ) CH ), 3.37 (6H, s, N–CH ), 3.51 (4H, m, N–C
2
C
Ar–H(3,5)), 7.39 (2H, t, Ar–H(4)), 7.66 (4H, d, Ar–H(2,6)). C
NMR (CDCl , 126 MHz, ppm): 48.00 (2C, N–CH ), 67.52 (2C,
2
2 2
3
3
3
3
1
). C NMR (CDCl
3
H
1
CH
2
CH
3.92 (2C, N–CH CH (CH ) CH )), 22.40 and 22.61 (4C, N–
2
(CH
2
)
2
CH
3
3
, 126 MHz, ppm):
Ph–CH ), 127.63 (2C, Ar–C(1)), 128.98 (4C, Ar–C(3,5)),
2
2
2
2 2
3
130.44 (2C, Ar–C(4)), 133.37 (4C, Ar–C(2,6)). ESI-TOF-MS:
+
2
CH
2
(CH
2
)
2
CH
3
), 28.40 (2C, N–CH
2
CH
2
(CH
2
)
2
CH
3
),
m/z calcd for C H NCl [M ꢀ Cl] : 226.16; found: 226.15.
1
6
20
5
TOF-MS: m/z calcd for C12
1.36 (2C, N–CH ), 64.09 (2C, N–CH CH (CH ) CH ). ESI-
2
Anal. calcd for C H NCl: C, 73.41; H, 7.70; N, 5.35; found:
16 20
C, 72.71; H, 7.84; N, 5.12.
3
2
2 2
3
+
H28NBr [M ꢀ Br] : 186.22; found:
1
found: C, 53.85; H, 10.56; N, 5.21.
86.19. Anal. calcd for C H NBr: C, 54.13; H, 10.60; N, 5.26;
1
2
28
Dimethyldi(4-methylbenzyl)ammonium chloride (10). Method
A. Reagents: 4-methylbenzyl chloride (9.15 ml, 69.00 mmol),
sodium carbonate (7.31 g, 69.00 mmol) and dimethylforma-
Dibenzyldimethylammonium bromide (5). Method A. Re-
agents: benzyl bromide (6.21 ml, 52.25 mmol), potassium
carbonate (7.22 g, 52.25 mmol) and dimethylformamide (30
mide (30 ml). Reaction temperature 80 1C and reaction time
1
72 h. Yield (white powder): 6.18 g (62%). H NMR (CDCl
3
,
ml). Reaction temperature 80 1C and reaction time 48 h. Yield
500 MHz, ppm): 2.33 (6H, s, CH
s, Ph–CH ), 7.16 (4H, d, Ar–H), 7.51 (4H, d, Ar–H). C NMR
3 3
), 3.09 (6H, s, CH ), 5.06 (4H,
1
white powder): 4.12 g (52%). H NMR (DMSO, 500 MHz,
), 4.70 (4H, s, Ph–CH ), 7.50–7.57
13
(
ppm): 2.89 (6H, s, N–CH
2
3
2
(CDCl
67.49 (2C, Ph–CH ), 124.53 (2C, Ar–C), 129.72 (4C, Ar–C),
3 3 3
, 126 MHz, ppm): 21.23 (2C, CH ), 47.96 (2C, CH ),
1
3
6H, m, Ar–H), 7.61–7.63 (4H, m, Ar–H). C NMR (DMSO,
(
2
1
428
N e w J . C h e m . , 2 0 0 4 , 2 8 , 1 4 2 6 – 1 4 3 0