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Chapter – 1 Preparation and Yield optimization.....
protons should give singlet at this chemical shift but these two protons
will couple with three protons of methyl group (C12) and will show
multiplet. In this case, some of the peaks have been merged to each
other and thus it showed triplet.
6. Rests of the peaks are due to the aromatic protons, where two
aromatic protons of methine groups (C15 & C19) gave multiplet at 6.68 δ
ppm. Two protons of methine groups (C6 & C8) gave multiplet at 6.93 δ
ppm while another two aromatic protons (C9 & C17) gave multiplet at
7.05 δ ppm. Rests of the three protons (C7, C16 & C18) gave multiplet at
7.25 δ ppm. Due to the unusual splitting J values could not be
calculated.
13 C NMR spectral interpretation of 2-methyl-1-(morpholin-4-ylmethyl)
indoline (DNJ-206)
1. C13 carbon atom became most shielded and showed chemical shift at
19.67 δ ppm.
2. Methylene group of C3 carbon atom gave peak at 37.58 δ ppm.
3. Methyl group attached to the aromatic nitrogen atom N11 showed
chemical shift at 38.16 δ ppm.
4. C2 carbon attached to the methyl group C13 gave peak at 59.01 δ ppm.
5. Bridged methylene C10 carbon gave peak in down field at 65.80 δ ppm
comparatively to other methylene groups due to the two nitrogen atoms
of aromatic ring and indoline ring.
6. 107.17, 117.90, 124.12, 126.69, 129.28 and 151.30 δ ppm chemical
shifts are due to the aromatic carbon atoms of phenyl ring of indoline
C6, C8, C9, C7, C4 and C5 respectively.
7. C15 and C19 carbons of aromatic ring attached to the nitrogen N11
showed chemical shift at 112.53 δ ppm. While another two carbons C16
and C18 showed chemical shift at 127.52 δ ppm.
8. 116.28 and 149.34 δ ppm chemical shifts are due to the carbon atoms
of the aromatic ring attached to the nitrogen atom N11 C17 and C14
respectively.
Department of Chemistry, Saurashtra University, Rajkot-360 005 52