Efficient one-pot alkylation of imines using nanosilver iodide in aqueous media

Article abstract of DOI:10.3906/kim-1201-40

An efficient ecofriendly method for the alkylation reaction of various imines is described by a simple one-pot reaction of aldehydes, amines and alkyl iodides in the presence of AgI nanoparticles in aqueous media. Silver iodide nanoparticles mediated an e

Full text of DOI:10.3906/kim-1201-40

Turk J Chem
36 (2012) , 852 – 859.
¨
˙
c
ꢀ TUBITAK
doi:10.3906/kim-1201-40
Efficient one-pot alkylation of imines using nanosilver
iodide in aqueous media
Javad SAFAEI-GHOMI1,∗, Ahmad KAKAVAND-QALENOEI1,
Mohammad Ali GHASEMZADEH1, Masoud SALAVATI-NIASARI2
1Department of Organic Chemistry, Faculty of Chemistry, University of Kashan,
51167 Kashan - IRAN
e-mail: safaei@kashanu.ac.ir
2Institute of Nano Science and Nano Technology, University of Kashan,
Kashan, 51167 - IRAN
Received: 25.01.2012
An efficient ecofriendly method for the alkylation reaction of various imines is described by a simple
one-pot reaction of aldehydes, amines and alkyl iodides in the presence of AgI nanoparticles in aqueous
media. Silver iodide nanoparticles mediated an enhanced rate and facility of reaction and showed high
influence in the green synthesis of some amine derivatives. Moreover, this nanoparticle increased the yields
of products and decreased the reaction times in all cases. The heterogeneous mediator was fully characterized
by scanning electron microscopy (SEM), X-ray diffraction (XRD), and FT-IR experimental techniques.
Key Words: Imine, alkylation, nanoparticles, amine, aqueous media, heterogeneous mediator, one-pot
reaction
Introduction
The transformation of imine to amine is an important reaction in current organic chemistry. Amines are im-
portant building blocks for pharmaceutical and chemical production.1−4 In recent years, there has been great
interest in the development of organic reactions in aqueous media.5,6 The use of water as solvent in organic re-
actions has many advantages from both economic and environmental aspects.7 Preparation of alkylated amines
from imines was reported by several methods. In one method aldehydes and amines were reacted in the presence
∗Corresponding author
852

Efficient one-pot alkylation of imines using nanosilver..., J. SAFAEI-GHOMI, et al.
of L-proline as organocatalyst.8 The other method is synthesis of secondary amine derivatives under conden-
sation of diethyl phosphonate, amine, and aldehyde with lanthanide triflate catalysis.9 Chiral propargylamines
also can be prepared by 1-pot 3-component reaction between an alkyne, an aldehyde, and a secondary amine
at room temperature in the presence of CuBr and (R)-quinap as catalyst.10 Recently, Barbier-type alkyla-
tion reactions have been extensively studied with aldehydes, ketones, imines, acetals, and nitriles. 11,12 The
Barbier-Grignard reaction using metallic mediates and alkyl halides in water is one of the most useful and
convenient methods for performing alkylation reactions. Most of the metal-mediated alkylation reactions of
imines were reported using indium, silver, or zinc as mediates.13,14 Recently, it was reported that the combina-
tion Zn/AgI/InCl3 was an efficient system for alkylation reaction of imines using unactivated alkyl iodides in
water.15 Thus far, there has been no report of the Grignard-Barbier-type allylation of imines using nanoparti-
cles as mediate in aqueous media. The higher efficiency of nanoparticles as mediate in organic reactions under
mild conditions, in comparison with of traditional solid state catalysts, has been demonstrated.16 Nowadays
application of nanostructures is an important versatile method for the preparation of organic compounds. Re-
cently, nanoparticles are attracting great attention since they display homogeneous-like activities due to their
large surface areas relative to their bulk forms.17−20 It has been demonstrated to be efficient on nanoscale
materials for various useful chemical transformations for the synthesis of diverse organic compounds, such as
preparations of propargylamines,21,22 triazole derivatives,23 quinoxalines compounds,24 C-N cross coupling
reactions,25 alkyne-azide cycloadditions,26β-acetamido ketones/esters,27 and synthesis of diaryl sulphides.28
Herein, we wish to report a novel and efficient aqueous Barbier-Grignard-type alkylation of imines with
alkyl iodides in a zinc-nanosilver-indium chloride system. A series of experiments were carried out in an effort
to develop an improved procedure for the synthesis of secondary amine by 3-component coupling between
aldehydes, amines, and alkyl iodides in aqueous media (Scheme).
Ar'
O
1
Zn/AgI(np)/InCl3
r.t , H2O
NH
R I
3
Ar' NH2
2
Ar
R
Ar
H
4a-j
Scheme. Alkylation of imines using nanosilver iodide in aqueous media.
Experimental
Chemicals were purchased from Merck in high purity. All of the materials were of commercial reagent grade.
Flash-column chromatography was performed using Merck silica gel 60 with freshly distilled solvents. The NMR
spectra (1 H, 13 C) were recorded on a Bruker 400 Ultrashield spectrometer using TMS as an internal standard.
The FT-IR spectrum was recorded on a Magna-IR, spectrometer 550 Nicolet in KBr pellets in the range of
400-4000 cm−1 . Elemental analyses were performed using a Heraeus CHN-O-Rapid analyzer. Powder X-ray
diffraction (XRD) was carried out on a Philips diffractometer of X’pert Company with monochromatized Cu
˚
Kα radiation (λ = 1.5406 A). Microscopic morphology of the products was visualized by SEM (LEO 1455VP).
853

Efficient one-pot alkylation of imines using nanosilver..., J. SAFAEI-GHOMI, et al.
Preparation of silver iodide nanoparticle
A solution of 0.415 g of KI (25 × 10−4 mol) in 25 mL of distillated water was added dropwise to AgNO3
solution (0.425 g, 25 × 10−4 mol in 25 mL of distillated water) under ultrasound power in the presence of 0.2
g of SDS as surfactant. The yellow as-synthesized precipitate was separated by centrifugation and washed with
distillated water and ethanol to remove impurities several times and then dried
Typical procedure for zinc-silver iodide and zinc-(silver iodide nanoparticle) alkylation of imines
(4a-j)
A mixture of water (10 mL), aldehyde (0.5 mmol), amine (0.6 mmol), and InCl3 was stirred well in a round-
bottomed flask for 10 min at room temperature. Then zinc (3 mmol), AgI (2 mmol), or AgI nanoparticle (0.5
mmol) and alkyl iodide (2.5 mmol) were added sequentially to the reaction system. The reaction mixture was
stirred at room temperature at the times indicated in the Table. After completion of the reaction, the mixture
was extracted using ether, dried over anhydrous sodium sulfate, and filtered, and the solvent was evaporated in
vacuum to give the crude product. The product was separated using silica-gel column chromatography using
hexane:ethyl acetate (8:1) as eluent. The identity and purity of the product were confirmed by 1 H and 13 CNMR
spectroscopy.
N-Phenyl-(1-(p-bromophenyl)-1-cyclohexylmethyl)amine (4a)
IR (KBr, cm−1): 3423 (NH), 3050, 2923, 2851, 1600, 744, 691 (CH). 1 H-NMR (400 MHz, CDCl3) δ: d =
1.29-1.49 (m, 6H), 1.53-2.18 (m, 5H), 4.09 (d, J = 6.04 Hz, 1H), 4.12 (br s, 1H), 6.45-6.47 (d, J = 7.83 Hz,
2H), 6.61-6.65 (t, J = 7.31 Hz, 1H), 7.05-7.09 (t, 2H), 7.17-7.19 (d, 2H), 7.41-7.43 ppm (d, 2H). 13 C-NMR (100
MHz, CDCl3) δ: d = 147.42 (C), 141.78 (C), 131.33 (2CH), 129.11 (2CH), 120.44 (C), 128.99 (2CH), 117.25
(CH), 113.18 (2CH), 62.92 (CH), 44.81 (CH), 30.11 (CH2), 29.35 (CH2), 26.36 (CH2), 26.36 (CH2), 26.36
ppm (CH2). UV (CHCl3): λmax (nm) = 360, 270.
N-Phenyl-(1-(p-chlorophenyl)-1-cyclohexylmethyl)amine (4b)
IR (KBr, cm−1): 3424 (NH), 3050, 3020, 2852, 2926, 1600, 748, 692 (CH). 1 H-NMR (400 MHz, CDCl3) δ:
1.26-1.53 (m 6H), 1.57-1.94 (m 5H), 4.13 (d, J = 6/03Hz 1H) 4.09 (br s, 1H), 6.42-6.51 (d, J = 7.80 Hz, 2H),
6.61-6.65 (t, J = 7.32 Hz, 1H), 7.59-7.09 (t, 2 H), 7.22-7.24 (d, 2H), 7.27-7.28 ppm (d, 2H). 13 C-NMR (100
MHz, CDCl3) δ: d = 147.43 (C), 141.21 (C), 132.31 (C), 129.98 (2CH), 128.57 (2CH), 128.38 (2CH), 117.21
(CH), 113.17 (2CH), 62.58 (CH), 44.84 (CH), 30.10 (CH2), 29.35 (CH2), 26.35 (CH2), 26.35 (CH2), 26.35
ppm (CH2). UV (CHCl3): λmax (nm) = 365, 275.
N-Phenyl-(2-methyl-1-phenylpropyl)amine (4c)
IR (KBr, cm−1): 3416 (NH), 3049, 3016, 2852, 2924, 1602, 747, 691 (CH). 1 H-NMR (400 MHz, CDCl3) δ: d
= 1.21-1.34 (m, 1 H), 1.38-1.48 (m, 5H), 1.53-1.74 (m, 4H), 1.87-2 (m, 1H), 2.31 (s, 3H), 4.08 (s, 1H), 4.09 (s,
1H), 6.50 (d, J = 7.61 Hz, 2H), 6.59 (t, J = 7.30 Hz, 1H), 7.02-7.09 (m, 2H), 7.11-7.27 ppm (m, 5H). 13 C-NMR
(100 MHz, CDCl3) δ: d = 147.42 (C), 139.78 (C), 136.33 (C), 129.11 (2CH), 128.99 (2CH), 127.44 (2CH),
854

Efficient one-pot alkylation of imines using nanosilver..., J. SAFAEI-GHOMI, et al.
117.25 (CH), 113.18 (2CH), 62.92 (CH), 44.81 (CH), 30.11 (CH2), 29.35 (CH2), 26.36 (CH2), 26.36 (CH2),
26.36 (CH2), 21.16 ppm (CH3). UV (CHCl3): λmax (nm) = 363, 272.
N-Phenyl-(1-phenyl-1-cyclohexylmethyl)amine (4d)
IR (KBr, cm−1): 3415 (NH), 3054, 3023, 2853, 2923, 1601, 750, 698 (CH). 1 H-NMR (400 MHz, CDCl3) δ:
d = 1.11-1.21 (m, 5H), 1.46-1.56 (m, 1 H), 1.65-1.75 (m, 4H), 1.88-1.91 (m, 1H), 4.11 (d, J = 6.31 Hz, 1H),
4.13 (br s, 1H), 6.51 (d, J = 7.71 Hz, 2H), 6.60 (t, J = 7.46 Hz, 1H), 7.04-7.08 (m, 2H), 7.21-7.23 (m, 1H),
7.27-7.30 ppm (m, 4H). 13 C-NMR (100 MHz, CDCl3) δ: d = 147.34 (C), 141.21 (C), 129.11 (2CH), 128.28
(2CH), 127.17 (2CH), 126.48 (CH), 116.21 (CH), 113.17 (2CH), 62.85 (CH), 44.84 (CH), 30.10 (CH2), 29.35
(CH2), 26.35 (CH2), 26.35 (CH2), 26.35 ppm (CH2). UV (CHCl3): λmax (nm) = 340, 275.
N-Phenyl-(2-methyl-1-phenylpropyl)amine (4e)
IR (KBr, cm−1): 3418 (NH), 3051, 3020.66, 2852, 2924, 1601, 755, 698 (CH). 1 H-NMR (400 MHz, CDCl3) δ:
d = 0.92-0.98 (d, J = 6.80 Hz, 3H), 1-1.01 (d, J = 6.77 Hz, 3H), 1.16-1.37 (m, 1H), 4.13 (s, 1H), 4.15 (s, 1H),
6.51 (d, J = 7.61 Hz, 2H), 6.63 (t, J = 7.31 Hz, 1H), 7.06-7.10 (m, 2H), 7.22-7.32 ppm (m, 5H). 13 C-NMR (100
MHz, CDCl3) δ: d = 147.23 (C), 141.13 (C), 129.31 (2CH), 128.98 (2CH), 128.57 (CH), 128.38 (CH), 126.21
(CH), 117.22 (CH), 113.31 (2CH), 63.85 (CH), 34.84 (CH), 19.70 (CH3), 18.55 ppm (CH3). UV (CHCl3):
λmax (nm) = 365, 270.
N-(p-Chlorophenyl)-(1-phenyl-1-cyclohexylmethyl)amine (4f)
IR (KBr, cm−1): 3410 (NH), 3050, 3020, 285.96, 2924, 1663, 703 (CH). 1 H-NMR (400 MHz, CDCl3) δ: d =
1.13-1.34 (m, 5 H), 1.51-1.54 (m, 1H), 1.64-1.77 (m, 4H), 1.87-2.18 (m, 1H), 4.09 (d, J = 6.16 Hz, 1H), 4.14
(br s, 1H), 6.41 (d, J = 8.79 Hz, 2H), 6.99 (d, J = 8.79 Hz, 2H), 7.22-7.32 ppm (m, 5H). 13 C-NMR (100
MHz, CDCl3) δ: d = 146.29 (C), 142.10 (C), 128.84 (2CH), 128.82 (2CH), 127.17 (2CH), 126.91 (CH), 121.47
(C), 114.25 (2CH), 63.55 (CH), 44.81 (CH), 30.20 (CH2), 29.50 (CH2), 26.40 (CH2), 26.35 (CH2), 26.31 ppm
(CH2). UV (CHCl3): λmax (nm) = 347, 275.
N-(m-Chlorophenyl)(1-phenyl-1-cyclohexylmethyl)amine (4g)
IR (KBr, cm−1): 3419 (NH), 3061, 3026, 2852, 2926, 1597, 759, 639 (CH). 1 H-NMR (400 MHz, CDCl3) δ:
0.89-1.09 (m, 5 H), 1.17-1.26 (m, 1H), 1.56-1.66 (m, 4H), 1.75-1.86 (m, 1H), 2.13 (s, 3H), 4.08-4.23 (m, 2 H), 6.36
(d, J = 7.90 Hz, 1H), 6.48 (s, 1H), 6.56 (d, J = 7.30 Hz, 1H), 6.95 (t, J = 7.70 Hz, 1H), 7.26-7.41 ppm (m, 5H).
13 C-NMR (100 MHz, CDCl3) δ: 148.85 (C), 146.7 (C), 141.98 (C) 130.01 (CH), 128.30 (CH), 127.11 (2CH),
127.10 (CH), 126.96 (CH), 116.82 (CH), 112.93 (CH), 111.30 (CH), 63.26 (CH), 44.77 (CH), 30.20 (CH2), 29.44
(CH2), 26.83 (CH2), 26.36 (CH2), 26.36 ppm (CH2). UV (CHCl3): λmax (nm) = 365, 270. Anal. Calcd. for
C19 H22 ClN: C 76.11, H 7.40, N 4.67. Found C 76.08, H 7.45, N 4.63.
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Efficient one-pot alkylation of imines using nanosilver..., J. SAFAEI-GHOMI, et al.
N-(p-bromophenyl)-(1-phenyl-1-cyclohexylmethyl)amine (4h)
IR (KBr, cm−1): 3422 (NH), 3051, 3025, 2852, 2925, 1593, 755, 701 (CH). 1 H-NMR (400 MHz, CDCl3) δ:
d = 1.42-1.47 (m, 5 H), 1.50-1.57 (m, 1H), 1.64-1.75 (m, 4H), 1.85-1.98 (m, 1H), 4.05 (d, J = 6.07 Hz, 1H),
4.19 (br s, 1H), 6.36 (d, J = 8.4 Hz, 2H), 7.13 (d, J = 8.8 Hz, 2H), 7.22-7.35 ppm (m, 5H). 13 C-NMR (100
MHz, CDCl3) δ: d = 146.66 (C), 142.15 (C), 128.90 (2CH), 128.28 (2CH), 127.15 (2CH), 126.93 (CH), 121.50
(C), 114.25 (2CH), 63.43 (CH), 44.78 (CH), 30.16 (CH2), 29.45 (CH2), 26.36 (CH2), 26.32 (CH2), 26.32 ppm
(CH2). UV (CHCl3): λmax (nm) = 335, 255. Anal. Calcd. for C19 H22 BrN: C 66.28, H 6.44, N 4.07. Found
C 66.32, H 6.46, N 4.01.
N-(m-Chlorophenyl)-(2-methyl-1-phenylpropyl)amine (4i)
IR (KBr, cm−1): 3421 (NH), 3052, 3027, 2926, 2960, 1597, 748, 697 (CH). 1 H-NMR (400 MHz, CDCl3) δ:
1.67 (d, J = 6.78 Hz, 3H), 1.32 (d, J = 6.72 Hz, 3H), 1.01-2.05 (m, 1 H), 4.07 (d, J = 6.16 Hz, 1 H), 4.14
(br s, 1H), 6.43 (d, J = 8.79 Hz, 2H), 6.91 (d, J = 8.8 Hz, 2H), 7.33-7.50 ppm (m, 5H). 13 C-NMR (100 MHz,
CDCl3) δ:d = 146.21 (C), 142.01 (C), 129.25 (2CH), 128.86 (2CH), 128.28 (2CH), 127.12 (CH), 121.42 (C),
114.29 (2CH), 63.91 (CH), 34.83 (CH), 19.66 (CH3), 18.63 ppm (CH3). UV (CHCl3): λmax (nm) = 350, 255.
Anal. Calcd. for C16 H18 ClN: C 73.98, H 6.98, N 5.39. Found C 73.94, H 6.97, N 5.43.
N-Benzyl-(1-(p-methylphenyl)-1-cyclohexylmethyl)amine (4j)
IR (KBr, cm−1): 3409 (NH), 3051, 3025, 2853, 2923, 1602, 750, 693 (CH). 1 H-NMR (400 MHz, CDCl3) δ: d
= 1.34-1.13 (m, 5 H), 1.39-1.70 (m, 6H), 1.96-1.98 (m, 1H), 2.37 (s, 3 H), 3.33 (d, J = 7.12 Hz, 1 H), 3.46 (d,
J = 13.23 Hz, 1 H), 3.66 (d, J = 13.5 Hz, 1 H), 7.13-7.54 ppm (m, 9H). 13 C-NMR (100 MHz, CDCl3) δ: d
= 141.13 (C), 139.91 (C), 136.31 (C), 128.98 (2CH), 128.57 (2CH), 128.38 (2CH), 128.3 (2CH), 126.21 (CH),
67.58 (CH), 51.74 (CH2 ), 44.84 (CH), 30.10 (CH2), 29.55 (CH2), 26.35 (CH2), 26.35 (CH2), 26.35 (CH2),
21.10 ppm (CH3). UV (CHCl3): λmax (nm) = 360, 257.
Results and discussion
Among the different metals investigated, indium, zinc, and silver were observed to be effective metals for the
alkylation reactions of imines to the corresponding amines in aqueous media.15 We carried out the one-pot
Barbier–Grignard-type alkylation reaction of simple imines by using Zn/AgI(np)/InCl3 in water. The scope
and versatility of the present reaction were investigated by using various aldehydes, amines, and alkyl iodides.
It was found that both primary aliphatic and aromatic amines were able to react smoothly to afford the
corresponding amines in good yields. This reaction is an efficient method for alkylation of imines so that yield
is up to 90%, as shown in the Table. Utilization of AgI nanoparticles increased the yield of the reaction and
also decreased the time of reaction impressively. The usage of nanoparticles as mediates has a very remarkable
effect on the reaction and so we can achieve even 97% yield in 9 h (entry b, Table). Nanoparticles are well
dispersed in solvent and so the reactant reaches the active site by diffusion. The comparison between time of
reaction in the presence of AgI nanoparticles and bulk AgI is shown in the Table.
856

Efficient one-pot alkylation of imines using nanosilver..., J. SAFAEI-GHOMI, et al.
Table. Zinc-silver iodide mediated alkylation reaction of imines in water. c
Entry
Ar
p-BrC6H4
p-ClC6H4
p-CH3C6H4
C6H5
Arꢀ
C6H5
R
Time[h]/Yield[%]a Yield [%]b in 24 h
a
b
c
d
e
f
C6H11
C6H11
C6H11
C6H11
C3H7
C6H11
C6H11
C6H11
C3H7
10/95
9/97
8315
8515
8215
7615
4315
65d, 15
78d
C6H5
C6H5
10/93
12/90
16/60
11/75d
13/92d
14/75
16/62
17/72d,e
C6H5
C6H5
C6H5
C6H5
p-ClC6H4
m-ClC6H4
p-BrC6H4
m-ClC6H4
g
h
i
C6H5
C6H5
60
C6H5
48
53d,e, 15
j
p-CH3C6H4 CH2(C6H5) C6H11
a In presence of AgI nanoparticles. b In presence of bulk AgI. c Unless otherwise noted, the reaction was carried out at
room temperature for 24 h. d By using MeOH/H2 O 1:1. e By using 2 equiv. of amine.
In order to investigate the morphology and particle size of AgI nanoparticles, a SEM image of AgI
nanoparticles was recorded and is presented in Figure 1. These results show that spherical AgI nanoparticles
were obtained from AgNO3 and KI with particle size 45-50 nm under ultrasound power.
Figure 1. SEM images of AgI nanoparticles.
Figure 2 shows the FT-IR spectrum of AgI nanoparticles. The broad peaks at 3436 and 1628 cm−1 can
be attributed to the ν (OH) stretching and bending vibrations, respectively. Thus, these peaks indicate the
presence of physisorbed water linked to nanoparticles.
857

Efficient one-pot alkylation of imines using nanosilver..., J. SAFAEI-GHOMI, et al.
Figure 2. FT-IR spectrum of AgI nanoparticles.
As shown in Figure 2, a peak corresponding to CH2 stretching vibration of SDS (sodium dodecyl
sulfonate) at 2923 cm−1 can be seen. The appearance of this peak suggests that a trace amount of SDS
was coated on the surface of AgI nanoparticles.
Figure 3 shows the XRD pattern of AgI nanoparticles. All reflection peaks in Figure 1 can be readily
indexed to the pure cubic phase of AgI with F-43m space group (JCDPS No. 78-0641). The crystallite size
diameter (D) of the AgI nanoparticles was calculated by the Debye–Scherrer equation (D = Kλ/βcosθ), where
β FWHM (full-width at half-maximum or half-width) is in radians and θ is the position of the maximum of
diffraction peak, K is the so-called shape factor, which usually takes a value of about 0.9, and k is the X-ray
˚
wavelength (1.5406 A for Cu Kα). Crystallite size of AgI was found to be 48 nm.
Figure 3. The XRD pattern of AgI nanoparticles.
Conclusions
An efficient, facile, and economical method for the alkylation of imines has been developed using AgI-
nanoparticles as the mediator in aqueous media. The products were obtained in excellent yields and the reaction
times were significantly reduced in comparison to using bulk silver iodide. The present protocol represents a
simple method for C-N bond formation in order to prepare some amines derivatives in the presence of novel
nanoscale materials.
858

Efficient one-pot alkylation of imines using nanosilver..., J. SAFAEI-GHOMI, et al.
Acknowledgments
The authors are grateful to University of Kashan for supporting this work by grant no: 65384. Also we thank
Prof Stephen G Pyne for his help.
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