Efficient synthesis of symmetrical N,N′-alkylidene bisamides catalysed by acetyl chloride

Article abstract of DOI:10.3184/174751913X13843645135577

Symmetrical bisamides were synthesised from aldehydes and amides in the presence of distilled acetyl chloride. The reaction is rapid, clean and gives the products in excellent yields.

Full text of DOI:10.3184/174751913X13843645135577

JOURNAL OF CHEMICAL RESEARCH 2013
DECEMBER, 751–753
RESEARCH PAPER 751
Efficient synthesis of symmetrical N,N’-alkylidene bisamides catalysed by
acetyl chloride
Hossein Mehrabi* and Elham Kanani
Department of Chemistry, Vali-e-Asr University of Rafsanjan, Rafsanjan 77176, Iran
Symmetrical bisamides were synthesised from aldehydes and amides in the presence of distilled acetyl chloride. The reaction
is rapid, clean and gives the products in excellent yields.
Keywords: symmetrical bisamides, aldehydes, amides, acetyl chloride
Bisamides are of considerable interest in the synthesis of
peptidomimetic compounds.1 Specifically, bisamides are key
fragments for the introduction of gem-diaminoalkyl residues
in retro-inverso pseudopeptide derivatives2,3 by treating the
corresponding amide with iodobenzene bis(trifluoroacetate).4,5
A literature survey revealed that a number of methods have
been reported for the synthesis of bisamides,6–14 using acidic
catalysts such as sulfuric acid,8 triflic acid,9 chlorosulfonic
acid,10 sulfamic acid,11 phosphotungstic acid,12 silica supported
polyphosphoric acid,13 and molybdate and silica sulfuric acids.14
Some of these procedures require long reaction times, give
low yields of product and have tedious work-up procedures.
We now report a highly efficient method for the synthesis of
symmetrical bisamides in excellent yields from aldehydes with
two equivalents of amides using distilled acetyl chloride at
room temperature (Scheme 1).
Inourinitialstudy, wechosethereactionof4-nitrobenzaldehyde
(1d, 1mmol) with acetamide (2d, 2 mmol) in the presence of
distilled acetyl chloride (1 mmol) in dry acetonitrile (10 mL).
The mixture was stirred at room temperature for 5 min. After
pouring the reaction mixture into water the product 3d was
obtained as a white solid in an excellent yield of 95%. We next
investigated the scope and generality of this transformation with
various aldehydes and aliphatic or aromatic amides (Table 1).
As can be seen from Table 1, the nature of the aldehyde was
important. When benzaldehyde derivatives especially with
electron-withdrawing groups such as nitro or halogen groups
(Table 1, entries 3d–g and 3j) were employed, a lower reaction
timewasrequiredthanforaldehydessuchasphenylacetaldehyde
or 3-phenylpropionaldehyde (Table 1, entries 3l–o).
Compounds 3a–i and 3m–o have been reported previously
in the literature,5,7,10,13–20 and were characterised by comparison
of their melting points and spectroscopic data with authentic
samples. The structures of other compounds were confirmed by
13
their spectra (1H NMR, C NMR, IR) and elemental analysis.
For example, the 1H NMR spectra of the compounds exhibited
a peak around δꢀ=6.39–6.64 ppm for the methine proton and
a peak around δꢀ=8.45–8.69 ppm for the NH protons. In the
IR spectra, the NH groups were observed at around 3265–
3286 cm–1 and the O=C-NH groups around 1662–1674 cm–1.
A possible mechanism for this reaction is suggested in
Scheme 2. Because of the presence of hydrochloric acid in
acetyl chloride as supplied and its probable interference with
the reaction, we used distilled acetyl chloride under anhydrous
conditions. Initially, acetyl chloride acted as a Lewis acid to
activate aldehyde 1 by complexation with aldehyde oxygen.
Complex 4 and amide form their corresponding hemiaminal
5 by a nucleophilic addition reaction. Following loss of
O
R1
O
O
O
Distilled CH3COCl
Dry CH3CN, r.t.
R2
N
H
N
H
R2
+
R2
NH2
R1
H
1 a-o
2 a-o
3 a-o
Scheme 1
Table 1 Synthesis of bisamides by the reaction between aldehydes and amides promoted by distilled acetyl chloride at room temperature
Comp.
3a
3b
3c
3d
3e
3f
3g
3h
3i
3j
3k
3l
3m
3n
3o
R1
R2
Reaction time/min
Yield/%a
97
90
93
95
88
90
93
98
97
95
95
85
90
80
83
Melting point/°C/(lit.)
238–240
Ph
Ph
Ph
CH3
8
10
10
5
5
5
(242)7
CH3CH2
Ph
207–21014
234–236
271–273
235–238
257–259
261–263
270–272
226–228
262–263
277–278
174–176
204–206
180–183
240–241
(237–238)5
(272)15
4-NO2C6H4
3-NO2C6H4
4-F C6H4
4-Cl C6H4
4-Me C6H4
4-MeO C6H4
2,4-Cl2C6H3
4-(Me)2N C6H4
PhCH2
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
(231–233)10
(259–261)13
(260–261)16
(274)17
8
10
10
5
10
15
18
25
20
(230–231)18
CH3
CH3
PhCH2CH2
PhCH2CH2
PhCH2CH2
(206–207)19
(198–199)20
(244–245)20
CH3CH2
Ph
aYields relate to isolated pure products.
* Correspondent. E-mail: mehraby_h@yahoo.com
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752 JOURNAL OF CHEMICAL RESEARCH 2013
COMe
H
OCOMe
N
O
Me
Cl
O
O
O
R1
R2
R2
O
H2N
R1
R1
H
H
4
5
1
MeCOOH
O
R1
O
O
O
R2
NH2
R1
N
R2
R2
N
H
N
H
R2
6
3
Scheme 2
N-(Phenyl-benzoylamino-methyl)benzamideꢀ (3c):ꢀ White solid, IR
(KBr) (vmax cm–1): 3289 (NH), 3108, 1667 (C=O), 1502, 1393, 1187, 1080.
1H NMR (500 MHz, d6‑DMSO): δ 6.47 (1H, t,ꢀJ=7.8 Hz, CH), 7.22–7.79
(15H, m, aromatic), 8.53 (2H, d, Jꢀ=7.8 Hz, 2NH). 13C NMR (125 MHz,
d6‑DMSO): δ 56.9 (CH), 126.3, 127.3, 129.4, 130.6, 130.9, 131.3, 133.8
and 134.7 (phenyl moiety), 167.2 (2C=O). Anal. Calcd for C21H18N2O2: C,
76.34; H, 5.49; N, 8.48. Found: C, 77.03; H, 5.57; N, 8.37%.
N-[Acetylamino(4-nitrophenyl)methyl]acetamideꢀ (3d): White solid,
IR (KBr) (vmax cm–1): 3317 (NH), 3108, 1668 (C=O), 1514, 1373, 1219,
1199, 1083. 1H NMR (500 MHz, d6‑DMSO): δ 2.08 (6H, s,ꢀ2CH3), 6.17
(1H, t,ꢀJ=8.0 Hz, CH), 7.35 (2H, d, J=7.4 Hz, aromatic), 7.94 (2H, d,
J=7.4 Hz, aromatic), 8.47 (2H, d, J=8.0 Hz, 2NH). 13C NMR (125 MHz,
d6‑DMSO): δ 26.3 (2CH3), 58.3 (CH), 129.7, 131.4, 135.6 and 143.6
(phenyl moiety), 161.2 (2C=O). Anal. Calcd for C11H13N3O4: C, 52.59; H,
5.22; N, 16.73. Found: C, 53.18; H, 5.30; N, 16.48%.
MeCOOH, reactive intermediate 6 is formed. Finally, a second
amide molecule attacks intermediate 6 as a nucleophile to
afford the final product 3 (Scheme 2).
In conclusion, we report here a simple one-pot reaction
between aldehydes and amides in the presence of distilled acetyl
chloride for the synthesis of symmetrical bisamide derivatives
at room temperature. The present protocol offers several
advantages including a clean and simple reaction procedure,
isolation of products by crystallisation, without employing
purification methods such as column chromatography, high
yields and short reaction times.
Experimental
All melting points were obtained in a Bamslead Electrothermal
9200 apparatus and are uncorrected. They are reported in Table 1.
All chemicals were purchased from Aldrich and Merck with high-
grade quality and used without any purification. The reactions
were monitored by TLC and all yields refer to isolated products.
1H and 13C NMR spectra were recorded in DMSO on a Bruker
500 MHz spectrometer. IR spectra were recorded by Bruker FT-IR
Equinax-55 spectrophotometer on KBr discs. Elemental analyses were
performed using a Carlo Erba EA 1108 instrument. All products were
characterised by their spectroscopic and physical data.
N-[Acetylamino(3-nitrophenyl)methyl]acetamideꢀ
(3e):
White
solid, IR (KBr) (vmax cm–1): 3307 (NH), 3115, 1672 (C=O), 1502, 1372,
1208, 1093. 1H NMR (500 MHz, d6‑DMSO): δ 2.02 (6H, s,ꢀ 2CH3),
6.25 (1H, t,ꢀJ=8.0 Hz, CH), 7.16 (1H, d, J=7.4 Hz, aromatic), 7.16 (1H,
t, J=7.4 Hz, aromatic), 7.38 (1H, d, J=7.4 Hz, aromatic), 7.86 (1H, d,
J=7.4 Hz, aromatic), 8.52 (2H, d, J=7.4 Hz, 2NH). 13C NMR (125 MHz,
d6‑DMSO): δ 26.1 (2CH3), 58.6 (CH), 127.2, 129.5, 130.0, 132.7, 135.2
and 140.7 (phenyl moiety), 168.1 (2C=O). Anal. Calcd for C11H13N3O4: C,
52.59; H, 5.22; N, 16.73. Found: C, 52.93; H, 5.35; N, 16.61%.
N-[Acetylamino(4-fluorophenyl)methyl]acetamideꢀ (3f): White solid,
IR (KBr) (vmax cm–1): 3280 (NH), 3104, 1665 (C=O), 1514, 1350, 1197,
1089, 825. 1H NMR (500 MHz, d6‑DMSO): δ 1.79 (6H, s, 2CH3), 6.54 (1H,
t, J=7.4 Hz, CH), 7.39–7.74 (4H, m, aromatic), 8.61 (2H, d, J=7.4 Hz,
2NH). 13C NMR (125 MHz, d6‑DMSO): δ 23.5 (2CH3), 56.7 (CH), 128.5,
129.9, 132.7 and 135.4 (phenyl moiety), 165.5 (2C=O). Anal. Calcd for
C11H13FN2O2: C, 58.92; H, 5.84; N, 12.49. Found: C, 59.09; H, 5.82; N,
12.46%.
Synthesisꢀ ofꢀ N-[phenyl(propionylamino)methyl]-propionamideꢀ (3b);ꢀ
typicalꢀprocedure
To a magnetically stirred mixture of benzaldehyde (1b, 1 mmol) and
distilled acetyl chloride (1 mmol) in dry acetonitrile (10 mL) was
added propionamide (2b, 2 mmol). The reaction was stirred at room
temperature for 10 min as mentioned in Table 1. The progress of the
reaction was followed by TLC. After the completion of the reaction, the
mixture was poured into water (20 mL). The solid product was filtered
and washed with water to give the pure product.
N-[Acetylamino(4-chlorophenyl)methyl]acetamideꢀ(3g): White solid,
IR (KBr) (vmax cm–1): 3291 (NH), 3113, 1679 (C=O), 1510, 1338, 1204,
N-[Phenyl(propionylamino)methyl]-propionamideꢀ (3b): White solid,
IR (KBr) (vmax cm–1): 3286 (NH), 3110, 1662 (C=O), 1504, 1363, 1194,
1
1073, 822. H NMR (500 MHz, d6‑DMSO): δ 1.82 (6H, s, 2CH3), 6.47
1
(1H, t, J=7.5 Hz, CH), 7.32 (2H, d, J=7.8 Hz, aromatic), 7.81 (2H, d,
J=7.8 Hz, aromatic), 8.53 (2H, d, J=7.5 Hz, 2NH). 13C NMR (125 MHz,
d6‑DMSO): δ 26.3 (2CH3), 54.7 (CH), 126.1, 128.3, 131.4 and 138.6
(phenyl moiety), 162.8 (2C=O). Anal. Calcd for C11H13ClN2O2: C, 54.89;
H, 5.44; N, 11.64. Found: C, 55.70; H, 5.56; N, 11.38%.
1085, 827. H NMR (500 MHz, d6‑DMSO): δ 1.21 (6H, t,ꢀ J=7.0 Hz),
2.14 (4H, q,ꢀ J=7.0 Hz), 6.39 (1H, t,ꢀ J=7.5 Hz, CH), 7.20–7.68 (5H,
m, aromatic), 8.67 (2H, d, Jꢀ=7.5 Hz, 2NH). 13C NMR (125 MHz,
d6‑DMSO): δ 20.7 (2CH3), 34.9 (2CH2), 54.3 (CH), 128.9, 131.3, 132.7
and 136.0 (phenyl moiety), 165.4 (2C=O). Anal. Calcd for C13H18N2O2: C,
66.64; H, 7.74; N, 11.96. Found: C, 66.79; H, 7.70; N, 11.90%.
N-[Phenyl(acetylamino)methyl]acetamideꢀ(3a):ꢀWhite solid, IR (KBr)
(vmax cm–1): 3315 (NH), 3087, 1661 (C=O), 1512, 1326, 1165, 1074, 822. 1H
NMR (500 MHz, d6‑DMSO): δ 1.88 (6H, s,ꢀ2CH3), 6.33 (1H, t,ꢀJ=7.5 Hz,
CH), 7.26–7.72 (5H, m, aromatic), 8.49 (2H, d, Jꢀ=7.5 Hz, 2NH). 13C NMR
(125 MHz, d6‑DMSO): δ 25.4 (2CH3), 52.8 (CH), 126.5, 130.7, 133.3 and
135.8 (phenyl moiety), 161.9 (2C=O). Anal. Calcd for C11H14N2O2: C,
64.06; H, 6.84; N, 13.58. Found: C, 64.47; H, 6.73; N, 13.37%.
N-[acetylamino(4-methylphenyl)methyl]acetamideꢀ(3h):ꢀWhite solid,
IR (KBr) (vmax cm–1): 3274 (NH), 3123, 1660 (C=O), 1532, 1357, 1237,
1
1183, 1081. H NMR (500 MHz, d6‑DMSO): δ 1.83 (6H, s, 2CH3), 1.97
(3H, s, CH3), 6.58 (1H, t, J=7.5 Hz, CH), 7.37–7.68 (4H, m, aromatic),
8.52 (2H, d, J=7.5 Hz, 2NH). 13C NMR (125 MHz, d6‑DMSO): δ 25.7
(2CH3), 31.4 (CH3), 54.3 (CH), 127.3, 128.6, 130.2 and 134.5 (phenyl
moiety), 163.7 (2C=O). Anal. Calcd for C12H16N2O2: C, 65.43; H, 7.32; N,
12.72. Found: C, 64.17; H, 7.19; N, 12.93%.
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JOURNAL OF CHEMICAL RESEARCH 2013 753
N-[Acetylamino(4-methoxyphenyl)methyl]acetamideꢀ (3i):ꢀ White
solid, IR (KBr) (vmax cm–1): 3306 (NH), 3122, 1673 (C=O), 1508, 1372,
1239, 1193, 1097. 1H NMR (500 MHz, d6‑DMSO): δ 1.86 (6H, s, 2CH3),
3.73 (3H, s, OCH3), 6.36 (1H, t, J=7.8 Hz, CH), 7.29 (2H, d, J=7.8 Hz,
aromatic), 7.94 (2H, d, J=7.8 Hz, aromatic), 8.47 (2H, d, J=7.8 Hz,
2NH). 13C NMR (125 MHz, d6‑DMSO): δ 27.2 (2CH3), 53.8 (CH), 58.4
(OCH3), 127.7, 129.2, 133.8 and 142.6 (phenyl moiety), 167.6 (2C=O).
Anal. Calcd for C12H16N2O3: C, 61.00; H, 6.83; N, 11.86. Found: C, 59.92;
H, 6.71; N, 11.84%.
N-[acetylamino(2,4-dichlorophenyl)methyl]acetamideꢀ (3j): White
solid, IR (KBr) (vmax cm–1): 3275 (NH), 3107, 1667 (C=O), 1518, 1352,
1194, 1094, 824. 1H NMR (500 MHz, d6‑DMSO): δ 1.82 (6H, s, 2CH3),
6.59 (1H, t, J=7.2 Hz, CH), 7.46–7.60 (3H, m, aromatic), 8.52 (2H, d,
J=7.2 Hz, 2NH). 13C NMR (125 MHz, d6‑DMSO): δ 22.2 (2CH3) 55.2
(CH), 127.1, 128.7, 129.2, 133.0, 133.1 and 136.9 (phenyl moiety), 168.4
(2C=O). Anal. Calcd for C11H12Cl2N2O2: C, 48.02; H, 4.40; N, 10.18.
Found: C, 48.17; H, 4.37; N, 10.14%.
13C NMR (125 MHz, d6‑DMSO): δ 23.7 (2CH3), 29.3 (2CH2), 31.1 (CH2),
37.8 (CH2), 56.7 (CH), 126.8, 128.2, 130.7 and 133.2 (phenyl moiety),
163.9 (2C=O). Anal. Calcd for C15H22N2O2: C, 68.67; H, 8.45; N, 10.68.
Found: C, 68.12; H, 8.62; N, 10.85%.
N-(1-Benzoylamino-3-phenylpropyl]benzamideꢀ(3o): White solid, IR
(KBr) (vmax cm–1): 3268 (NH), 3109, 1673 (C=O), 1512, 1352, 1091, 8244.
1H NMR (500 MHz, d6-DMSO): 2.54 (2H, t,ꢀJ=7.6 Hz, CH2), 2.82 (2H,
t,ꢀJ=7.6 Hz, CH2), 6.49 (1H, m, CH), 7.29–7.81 (15H, m, aromatic), 8.41
(2H, d, J=7.5 Hz, 2NH). 13C NMR (125 MHz, d6‑DMSO): δ 30.6 (CH2),
39.0 (CH2), 54.9 (CH), 127.4, 128.1, 129.2, 129.4, 130.3, 131.2 133.5 and
135.3 (phenyl moiety), 169.4 (2C=O). Anal. Calcd for C23H22N2O2: C,
77.07; H, 6.19; N, 7.82. Found: C, 77.83; H, 6.15; N, 7.73%.
Receivedꢀ19ꢀJulyꢀ2013;ꢀacceptedꢀ13ꢀOctoberꢀ2013
Paperꢀ1302071ꢀdoi:ꢀ10.3184/174751913X13843645135577
Publishedꢀonline:ꢀ6ꢀDecemberꢀ2013
N-[Acetylamino(4-dimethylaminophenyl)methyl]acetamideꢀ
(3k):ꢀ
White solid, IR (KBr) (vmax cm–1): 3283 (NH), 3113, 1669 (C=O), 1525,
References
1
1358, 1200, 1083, 815. H NMR (500 MHz, d6‑DMSO): δ 1.97 (6H,
1
2
C. Aleman and J. Puiggali, J.ꢀOrg.ꢀChem., 1995, 60, 910.
P.V. Pallai, R.S. Struthers, M. Goodman, L. Moroder, E. Wunsch and W.
Vale, Biochemistry, 1985, 24, 1933.
K.I. Nunami, T. Yamazaki and M. Goodman, Biopolymers, 1991, 31, 1503.
M. Rodriguez, P. Dubreuil, J.P. Bali and J. Martinez, J.ꢀMed.ꢀChem., 1987,
30, 758.
s, 2CH3), 2.73 (6H, s, N–CH3), 6.64 (1H, t, J=7.5 Hz, CH), 7.40–7.68
(4H, m, aromatic), 8.64 (2H, d, J=7.5 Hz, 2NH). 13C NMR (125 MHz,
d6‑DMSO): δ 24.6 (2CH3), 38.3 (N–CH3), 57.6 (CH), 127.9, 129.5, 131.6
and 134.7 (phenyl moiety), 166.9 (2C=O). Anal. Calcd for C13H19N3O2: C,
62.63; H, 7.68; N, 16.85. Found: C, 62.44; H, 7.73; N, 16.81%.
3
4
5
6
7
J. Pernak, M. Blazej and W. Jozef, Synthesis, 1994, 12, 1415.
E.R. Gilbert, Synthesis, 1972, 30.
A.R. Katritzky, W.Q. Fan, M. Black and J. Pernak, J.ꢀOrg.ꢀChem., 1992, 57,
547.
E.E. Magat, B.F. Faris, J.E. Reith and L.F. Salibury, J.ꢀAm.ꢀChem.ꢀSoc.,
1951, 73, 1028.
A.H. Fernandez, R.M. Alvarez and T.M. Abajo, Synthesis, 1996, 1299.
N-(1-Acetylamino-2-phenylethyl]acetamideꢀ (3l): White solid, IR
(KBr) (vmax cm–1): 3265 (NH), 3104, 1668 (C=O), 1510, 1352, 1094,
829. 1H NMR (500 MHz, d6‑DMSO): δ 1.83 (6H, s, 2CH3), 2.73 (2H, t,ꢀ
J=7.5 Hz, CH2), 6.42 (1H, m, CH), 7.41–7.85 (5H, m, aromatic), 8.69 (2H,
d, J=7.5 Hz, 2NH). 13C NMR (125 MHz, d6‑DMSO): δ 25.1 (2CH3), 32.8
(CH2), 57.2 (CH), 127.7, 129.5, 131.4 and 135.0 (phenyl moiety), 166.8
(2C=O). Anal. Calcd for C12H16N2O2: C, 65.43; H, 7.32; N, 12.72. Found:
C, 65.59; H, 7.27; N, 12.68%.
8
9
10 M.A. Abbasinejad, M.H. Mosslemin and A. Hassanabadi,ꢀJ.ꢀChem.ꢀRes.,
2009, 218.
11 N.P. Selvam, S. Saranya and P.T. Perumal,ꢀCan.ꢀJ.ꢀChem., 2008, 85, 32.
12 G. Harichandran, S.D. Amalraj and P. Shanmugam, IndianꢀJ.ꢀChem., 2011,
50B, 77.
13 M.R. Mohammad Shafiee, J.ꢀSaudiꢀChem.ꢀSoc., (in press).
14 F. Tamaddon, H. Kargar-Shooroki and A.A. Jafari, J.ꢀ Mol.ꢀ Catal.ꢀ A:ꢀ
Chem., 2013, 368–369, 66.
15 P.I. Ittegerah and K.C. Pandya, Proc.ꢀIndian.ꢀAcad.ꢀSci., 1942, 15A, 2725;
Chem.ꢀAbstr., 1943, 37, 2725.
16 S.W. Breuer, T. Bernarth and D. Ben-Ishai, Tetrahedron, 1967, 23, 2869.
17 R.K. Mehra and K.C. Pandya, Proc.ꢀ Indianꢀ Acad.ꢀ Sci., 1939, 9A, 508,
Chem.ꢀAbstr., 1939, 33, 8589.
18 R.K. Mehra and K.C. Pandya, Proc.ꢀIndian.ꢀAcad.ꢀSci., 1939, 10A, 285;
Chem.ꢀAbstr., 1940, 34, 1981.
19 N. Yanaihara and M. Saito, Chem.ꢀPharm.ꢀBull., 1967, 15, 128.
20 K.C. Pandya and R.R. Bhandari, J.ꢀ Indianꢀ Chem.ꢀ Soc., 1947, 24, 185,
Chem.ꢀAbstr., 1949, 43, 2600.
N-(1-Acetylamino-3-phenylpropyl]acetamideꢀ (3m): White solid,
IR (KBr) (vmax cm–1): 3273 (NH), 3102, 1669 (C=O), 1528, 1347, 1094,
827. 1H NMR (500 MHz, d6‑DMSO): δ 1.80 (6H, s, 2CH3), 2.56 (2H, t,ꢀ
J=7.5 Hz, CH2), 2.73 (2H, t,ꢀJ =7.5 Hz, CH2), 6.63 (1H, m, CH), 7.38–7.87
(5H, m, aromatic), 8.32 (2H, d, J=7.5 Hz, 2NH). 13C NMR (125 MHz,
d6‑DMSO): δ 24.7 (2CH3), 30.6 (CH2), 38.3 (CH2), 55.9 (CH), 126.7,
128.2, 130.7 and 133.6 (phenyl moiety), 162.2 (2C=O). Anal. Calcd
for C13H18N2O2: C, 66.64; H, 7.74; N, 11.96. Found: C, 67.73; H, 7.69; N,
11.86%.
N-(1-Propionylamino-3-phenylpropyl]propionamideꢀ(3n):White solid,
IR (KBr) (vmax cm–1): 3265 (NH), 3117, 1661 (C=O), 1510, 1357, 1094.
1H NMR (500 MHz, d6‑DMSO): δ 1.28 (6H, t,ꢀJ=7.0 Hz), 2.10 (4H, q,ꢀ
J=7.0 Hz), 2.78 (2H, t,ꢀJ=7.5 Hz, CH2), 2.89 (2H, t,ꢀJ=7.5 Hz, CH2), 6.40
(1H, m, CH), 7.43–7.89 (5H, m, aromatic), 8.47 (2H, d, J=7.5 Hz, 2NH).
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