Question

1.what are all the possible points of isomerism in duloxetine hydrochloride and assign stereodescriptors to any alkenes, chiral centres?

2. the infrared, mass spectroscopic and 1H and 13C NMR data for duloxetine hydrochloride

Answer 1

Answer on Question#59432 - Chemistry - Inorganic Chemistry

Question:

1. what are all the possible points of isomerism in duloxetine hydrochloride and assign stereodescriptors to any alkenes, chiral centres?

2. the infrared, mass spectroscopic and 1H and 13C NMR data for duloxetine hydrochloride

Solution:

Duloxetine hydrochloride is (+)-(S)-N-methyl-y-(1-naphthyloxy)-2-thiophenepropylamine hydrochloride. The empirical formula is C18H19NOS·HCl, which corresponds to a molecular weight of 333.88. The structural formula is:

Answer:

1) Duloxetine hydrochloride should R-isomer - (3R)-N-Methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine HCl:

Stereo descriptors alkenes to chiral centers are R and S.

2) Mass: M+297; $^{1}$ H-NMR (DMSO- $d_{6}$ ): δ 1.8 (m, 2H), 2.5 (s, 6H), 2.4-2.6 (m, 2H), 5.9-6.0 (m, 1H), 6.9-7.0 (m, 2H), 7.1-7.3 (m, 3 H), 7.4-7.6 (m, 3H), 7.9 (m, 1H), 8.2 (m, 1H)& IR (cm $^{-1}$ ): 780, 1091(Ether), 1395, 1583(Amine, bend), 2771, 2946, 3056(Amine, str).

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