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Chapter – 1 Preparation and Yield optimization.....
5. Another two methylene groups of morpholine ring C2 and C6 showed
chemical shift in the downfield at 67.05 δ ppm which is due to the
oxygen atom directly attached to both the methylene groups.
6. Bridged methylene C7 carbon gave peak in downfield at 71.45 δ ppm
comparatively to other methylene groups due to the two nitrogen atoms
of morpholine ring and indoline ring.
7. 77.86, 77.54 and 77.22 δ ppm are the characteristic peaks due to the
solvent CDCl3.
8. 107.13, 118.06, 124.22, 127.47, 152.47 and 170.84 δ ppm chemical
shifts are due to the aromatic carbon atoms of phenyl ring C13, C15, C16,
C14, C11 and C12 respectively.
Peaks obtained in the DEPT-135 were in the agreement of the carbons
present in the molecule.
1 H NMR spectral interpretation of 2-methyl-1-(morpholin-4-ylmethyl)
indoline (DNJ-206)
1. Three most shielded protons of methyl group (C13) gave multiplet at
1.32 δ ppm. As discussed earlier, these protons should show their
multiplicity as doublet due to the presence of single proton at C2, but
two nitrogen atoms are present in the molecule and thus due to their
effect these methyl protons coupled with one proton of methane group
(C2) and another two protons of methylene group (C3) and gave
multiplet.
2. Two protons of methylene groups (C3) gave quartet at 2.59 δ ppm
which actually should give double doublet but it merged to give quartet.
3. Three protons of methyl group (C12) attached to the nitrogen atom gave
singlet at 2.85 δ ppm.
4. One proton of methine group (C2) gave quintet at 4.43 δ ppm which
actually should show multiplet due to the presence of three protons of
methyl group (C13) and two protons of methylene group (C3).
5. Two protons of methylene group (C10) became deshielded due to the
two nitrogen atoms and gave triplet at 4.76 δ ppm. Actually these two
Department of Chemistry, Saurashtra University, Rajkot-360 005 51