Arch. Pharm. Chem. Life Sci. 2008, 341, 247–261
Table 2. Continued
Synthesis and Local Anesthetic Activity of Novel Acetamides
255
Com-
pound
Code
IR (cm– 1) (KBr)
13C-NMR d (ppm) (DMSO-d6, TMS)
ESMS (Meth-
anol) m/z
Molecular
ion peak &
Fragment
22
3061.6 (Aromatic C-H str), 1091.5 (C-O of 1,3,4-oxa-
diazole nucleus), 1659.9 (C=N of 1,3,4-oxadiazole
nucleus), 1601.4 & 1502.3 (Aromatic C-C str), 1306.1
(C-N str tertiary amino group), 1690.8 (C=O str of
amide), 3371.0 (N-H str of amide), 2933.7 (Aliphatic
C-H str), 1433.5 (C-H def in CH3), 829.6 (C-H def di-sub-
stituted benzene ring), 3455.1 (O-H str of alcoholic
group), 1162.6 (C-O str of alcoholic group).
127.1 (C-29 & C-69), 129.3 (C-39 & C-59), 137.6 (C-49),
133.2 (C-19), 171.3 (C-2), 168.5 (C-5), 174.7 (NHCO-
CH2N), 57.9 (NHCOCH2N), 62.2 (OHCH2CH2N), 56.0
(OHCH2CH2N), 21.2 (CH3C6H5).
320, 118
23
24
3059.1 (Aromatic C-H str), 1092.3 (C-O of 1,3,4-oxa-
diazole nucleus), 1663.8 (C=N of 1,3,4-oxadiazole
nucleus), 1598.2 & 1500.3 (Aromatic C-C str), 1302.4
(C-N str tertiary amino group), 1694.3 (C=O str of
amide), 3374.9 (N-H str of amide), 2935.3 (Aliphatic
C-H str), 1432.2 (C-H def in CH3), 834.6 (C-H def di-
substituted benzene ring).
126.9 (C-29 & C-69), 129.4 (C-39 & C-59), 137.5 (C-49),
133.8 (C-19), 171.4 (C-2), 168.3 (C-5), 174.4 (NHCO-
CH2N), 57.8 (NHCOCH2N), 55.6 (C-a & C-d of morpho-
line), 71.3 (C-b & C-c of morpholine), 21.0 (CH3C6H5).
302, 100
397, 194
3062.8 (Aromatic C-H str), 1088.2 (C-O of 1,3,4-oxa-
diazole nucleus), 1661.9 (C=N of 1,3,4-oxadiazole
nucleus), 1596.9 & 1499.5 (Aromatic C-C str), 1299.7
(C-N str tertiary amino group), 1693.6 (C=O str of
amide), 3362.3 (N-H str of amide), 2932.4 (Aliphatic
C-H str), 1432.0 (Aliphatic C-H def), 830.6 (C-H def di-
substituted benzene ring), 2952.2 (C-H str of cyclo-
hexane).
126.8 (C-29 & C-69), 129.6 (C-39 & C-59), 137.2 (C-49),
133.7 (C-19), 171.7 (C-2), 168.3 (C-5), 174.5 (NHCO-
CH2N), 54.8 (NHCOCH2N), 27.4 ( C-c, C-e, C-c9 & C-e9 of
dicyclohexylamine), 30.8 ( C-b, C-f, C-b9 & C-f9 of
dicyclohexylamine), 22.7 (C-d & C-d9 of dicyclohexyl-
amine), 50.9 (C-a & C-a9 of dicyclohexylamine),
21.3 (CH3C6H5).
25
26
3063.4 (Aromatic C-H str), 1089.2 (C-O of 1,3,4-oxa-
diazole nucleus), 1659.1 (C=N of 1,3,4-oxadiazole
nucleus), 1601.3 & 1501.1 (Aromatic C-C str), 1302.4
(C-N str tertiary amino group), 1689.9 (C=O str of
amide), 3362.5 (N-H str of amide), 2934.3 (C-H str of CH3), C-f, C-b9 & C-f9 of dibenzylamine), 127.0 (C-d & C-d9 of
1432.1 (C-H def in CH3), 832.6 (C-H def di-substituted
benzene ring).
127.2 (C-29 & C-69), 129.5 (C-39 & C-59), 137.6 (C-49),
133.4 (C-19), 171.1 (C-2), 168.2 (C-5), 174.4 (NHCO-
CH2N), 57.1 (NHCOCH2N), 58.6 [N(CH2C6H5)], 128.5
(C-c, C-e, C-c9 & C-e9 of dibenzylamine), 129.3 (C-b,
412, 210
336, 134
dibenzylamine), 136.6 (C-a & C-a9 of dibenzylamine),
21.1 (CH3C6H5).
3063.3 (Aromatic C-H str), 1090.1 (C-O of 1,3,4-oxa-
diazole nucleus), 1661.4 (C=N of 1,3,4-oxadiazole
nucleus), 1599.1 & 1502.2 (Aromatic C-C str), 1302.9
(C-N str tertiary amino group), 1691.5 (C=O str of
amide), 3360.3 (N-H str of amide), 745.4 (C-H def dis-
ubstituted benzene ring), 2932.5 (Aliphatic C-H str),
1429.8 (C-H def in CH3), 830.8 (C-H def di-substituted
benzene ring).
127.1 (C-29 & C-69), 129.2 (C-39 & C-59), 137.4 (C-49),
133.3 (C-19), 171.4 (C-2), 168.2 (C-5), 174.7 (NHCO-
CH2N), 59.5 (NHCOCH2N), 38.3 [N(CH3)CH2C6H5],
61.2 [N(CH3)CH2C6H5], 128.6 (C-c, C-e of N-methyl-
benzylamine), 129.2 (C-b, C-f of N-methylbenzyl-
amine), 136.4 (C-a of N-methylbenzylamine), 127.1
(C-d of of N-methylbenzylamine), 21.2 (CH3C6H5).
27
28
3061.3 (Aromatic C-H str), 1091.3 (C-O of 1,3,4-oxa-
diazole nucleus), 1660.4 (C=N of 1,3,4-oxadiazole
nucleus), 1599.4 & 1498.8 (Aromatic C-C str), 1302.5
(C-N str tertiary amino group), 1693.1 (C=O str of
amide), 3360.9 (N-H str of amide), 2933.6 (C-H str in
CH3), 1432.1 (C-H def in CH3), 832.2 (C-H def di-substi-
tuted benzene ring), 2951.8 (C-H str in cyclohexane).
126.9 (C-29 & C-69), 129.4 (C-39 & C-59), 137.3 (C-49),
133.4 (C-19), 171.3 (C-2), 168.5 (C-5), 174.2 (NHCO-
CH2N), 57.9 (NHCOCH2N), 36.6 (N(CH3)C6H11), 27.1
(C-c & C-e of N-methylcyclohexylamine), 30.7 (C-b,
C-f of N-methylcyclohexylamine), 55.2 (C-a of N-meth-
ylcyclohexylamine), 22.8 (C-d of N-methylcyclohexyl-
amine), 20.0 (CH3C6H5).
328, 126
292, 86
3066.4 (Aromatic C-H str), 1092.0 (C-O of 1,3,4-oxa-
diazole nucleus), 1658.5 (C=N of 1,3,4-oxadiazole
nucleus), 1603.2 & 1502.6 (Aromatic C-C str), 1304.8
(C-N str tertiary amino group), 1689.3 (C=O str of
amide), 3361.4 (N-H str of amide), 830.6 (C-H def di-
substituted benzene ring), 2932.8 (Aliphatic C-H str),
1433.0 (Aliphatic C-H def), 1242.4 (C-F str).
128.4 (C-29 & C-69), 115.8 (C-39 & C-59), 162.6 (C-49),
132.0 (C-19), 171.8 (C-2), 168.3 (C-5), 174.9 (NHCO-
CH2N), 57.6 (NHCOCH2N), 13.4 (CH3CH2N), 46.2
(CH3CH2N).
i 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim