Electron Ionization (EI) Induced Mass Spectral Analysis of Substituted Phenylacetamides

MATERIALS AND METHODS
General method for the synthesis of amides
In a three neck round bottom flask, 1, 1’-carbonyldiimidazole (1.2 eq) was added to a solution of carboxylic acid (1 eq) 
in freshly distilled THF at RT. After complete consumption of carboxylic acid (TLC), amine (1.1 eq) was added and 
the reaction continued at room temperature. After completion of the reaction, reaction mixture was diluted with ethyl 
acetate and treated with 10% aqueous. NaOH solution (100 ml). The organic layer was separated and the aqueous 
layer was extracted with ethyl acetate. The combined organic phase was washed successively with 2 N HCl (100 
ml) and brine (100 ml), dried over anhydrous Na
2
SO
4 
and concentrated under reduced pressure. Pure amide was then 
obtained after flash chromatography (hexane-ethyl acetate).

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Gupta et al
Der Chemica Sinica, 2017, 8(1):218-222
Pelagia Research Library
219
Mass spectral analysis
The electron impact-mass spectrometric analysis (EI-MS) analysis was carried out on Agilent 6890 N GC-5973 
Quadrupole Mass Selective Detector equipped with BP-5 capillary column (30 m × 0.32 mm id, 0.25 µm film 
thickness). Ionization was done by electron impact at 70 eV and 230°C. Helium was used as the carrier gas at the 
flow rate of 1.0 ml/min.
Table 1: Mass spectral fragment ions appearing in the mass spectra of Piperidine and Morpholine derived substituted phenylacetamides 
Amide
M Wt
Fragment Ions m/z (Intensity)
1-(2-Phenylacetyl)piperidine
203
203 (48), 118 (3), 112 (100), 91 (20), 89 (3), 84 (10), 69 (42), 41 (10), 56 (6)
1-(2-(2-Methylphenyl)acetyl) piperidine
217 217 (68), 216 (2), 202 (9), 132 (2), 112 (100), 105 (22), 91 (2), 103 (7), 84 (9), 69 (36), 41 
(11), 77 (11), 56 (4)
1-(2-(3-Methylphenyl)acetyl) piperidine
217
217 (63), 216 (8), 202 (2), 132 (3), 112 (100), 105 (22), 91 (7), 103 (9), 84 (12), 69 (48), 
41 (14), 77 (12), 56 (7)
1-(2-(4-Methylphenyl)acetyl) piperidine
217 217 (55), 216 (7), 132 (4), 112 (100), 105 (22), 91 (2), 103 (7), 84 (9), 69 (44), 41 (11), 77 
(11), 56 (7)
1-(2-(2-Methoxyphenyl)acetyl) piperidine
233 233 (98), 232 (1), 202 (38), 148 (7), 132 (5), 112 (100), 121 (24), 91 (55), 119 (3), 84 (12), 
69 (67), 41 (15), 77 (8), 56 (6)
1-(2-(3-Methoxyphenyl)acetyl) piperidine
233 233 (77), 232 (12), 218 (2), 148 (4), 112 (100), 121 (17), 91 (12), 119 (2), 84 (10), 69 (39), 
41 (9), 78 (8), 56 (6)
1-(2-(4-Methoxyphenyl)acetyl) piperidine
233 233 (98), 232 (4), 148 (6), 132 (1), 112 (100), 121 (94), 91 (9), 119 (4), 84 (7), 69 (64), 41 
(14), 78 (14), 56 (7)
1-(2-(2-Fluorophenyl)acetyl) piperidine
221
221 (42), 220 (3), 202 (3), 136 (3), 112 (100), 109 (39), 107 (5), 84 (10), 69 (42), 41 (11), 
83 (11), 56 (6)
1-(2-(3-Fluorophenyl)acetyl) piperidine
221
221 (29), 220 (7), 136 (3), 112 (100), 109 (37), 107 (3), 84 (12), 69 (43), 41 (12), 83 (10), 
56 (7)
1-(2-(4-Fluorophenyl)acetyl) piperidine
221
221 (29), 220 (4), 136 (3), 112 (100), 109 (37), 107 (4), 84 (8), 69 (43), 41 (12), 83 (10), 
56 (6)
1-(2-(2-Methylphenyl)acetyl) morpholine
219 219 (97), 204 (9), 132 (13), 114 (100), 105 (55), 103 (14), 86 (8), 70 (54), 42 (7), 77 (14), 
56 (8)
1-(2-(3-Methylphenyl)acetyl) morpholine
219
219 (97), 132 (20), 176 (7), 114 (100), 105 (62), 103 (13), 86 (12), 70 (55), 42 (8), 77 
(14), 56 (12)
1-(2-(4-Methylphenyl)acetyl) morpholine
219
219 (58), 132 (10), 176 (2), 114 (100), 105 (42), 103 (8), 86 (6), 70 (38), 42 (6), 77 (6), 
56 (7)
1-(2-(2-Methoxyphenyl)acetyl) morpholine
235 235 (100), 204 (18), 148 (20), 114 (93), 121 (65), 91 (57), 119 (3), 86 (7), 70 (39), 42 (6), 
77 (6), 56 (7)
1-(2-(3-Methoxyphenyl)acetyl) morpholine
235
235 (73), 204 (2), 148 (25), 114 (100), 121 (40), 91 (15), 86 (11), 70 (44), 42 (5), 77 (6), 
56 (9)
1-(2-(4-Methoxyphenyl)acetyl) morpholine
235
235 (33), 148 (4), 114 (30), 121 (100), 91 (4), 86 (2), 70 (19), 42 (3), 77 (5), 56 (3)
1-(2-(4-Methylphenyl)acetyl)-2-
methylpiperidine
231 231 (50), 216 (1), 132 (4), 126 (100), 112 (2), 105 (28), 103 (6), 98 (12), 83 (12), 55 (12), 
91 (3), 70 (4)
1-(2-(4-Methylphenyl)acetyl)-3-
methylpiperidine
231
231 (69), 216 (3), 132 (3), 126 (100), 105 (24), 103 (5), 98 (9), 83 (12), 55 (20), 91 (3), 
70 (3)
1-(2-(4-Methylphenyl)acetyl)-4-
methylpiperidine
231
231 (46), 132 (4), 126 (100), 105 (23), 103 (4), 98 (4), 83 (17), 55 (25), 91 (3), 70 (4)