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Chapter – 1 Preparation and Yield optimization.....
1 H NMR spectral interpretation of 2-methyl-1-(morpholin-4-ylmethyl)
indoline (DNJ-102)
1. Three most shielded protons of methyl group (C17) gave multiplet at
1.28 δ ppm. Usually these protons should show their multiplicity as
doublet due to the presence of single proton at C9, but two nitrogen
atoms are present in the molecule and thus due to their effect these
methyl protons coupled with one proton of methine group (C9) and
another two protons of methylene group (C10) and gave multiplet.
2. Four protons of two morpholinyl methylene groups attached with the
nitrogen atom gave triplet at 2.45 δ ppm, while another four protons of
rest of the two morpholinyl methylene groups attached with the oxygen
atom gave triplet at 3.73 δ ppm.
3. Two protons of C10 carbon atom splitted into two which showed singlet
for each proton at 2.62 δ ppm and at 2.83 δ ppm respectively.
4. One proton of methine group (C9) gave quartet at 3.14 δ ppm which
actually should show multiplet due to the presence of three protons of
methyl group (C17) and two protons of methylene group (C10).
5. Two protons of methylene group (C7) became deshielded due to the
two nitrogen atoms and gave singlet at 4.44 δ ppm.
6. Two aromatic protons of C13 and C15 methine groups gave multiplet at
6.63 δ ppm while another two aromatic protons of C14 and C16 methine
groups gave multiplet at 7.00 δ ppm.
13 C NMR spectral interpretation of 2-methyl-1-(morpholin-4-ylmethyl)
indoline (DNJ-102)
1. Methyl group-C17 carbon gave peak at 14.35 δ ppm chemical shift.
2. 37.55 δ ppm chemical shift is due to the methylene group C10 carbon.
3. Two methylene groups of morpholine ring, C3 and C5 carbons gave
peak at 51.48 δ ppm chemical shift.
4. C9 carbon attached to the C17 methyl group and nitrogen atom of the
indoline ring showed chemical shift in downfield at 59.46 δ ppm due to
the adjacent nitrogen atom.
Department of Chemistry, Saurashtra University, Rajkot-360 005 50