DR ANTHONY MELVIN CRASTO

DR ANTHONY MELVIN CRASTO

ORGANIC CHEMISTRY EDUCATION

4,6,7,8,9,10-hexahydro-1H-6,10-methanopyrazino[2,3-h][3]benzazepine-2,3-dione.

 

 

An external file that holds a picture, illustration, etc. Object name is scipharm-2012-80-329f2.jpg

 

 

 

Chemical structures of Varenicline Tartrate and degradant product (DP-I).........4,6,7,8,9,10-hexahydro-1H-6,10-methanopyrazino[2,3-h][3]benzazepine-2,3-dione.

An external file that holds a picture, illustration, etc. Object name is scipharm-2012-80-329f4.jpg

(A) 1H NMR spectrum of DP-I. (B) Proton decoupled 13C NMR spectrum of DP-I.

 

An external file that holds a picture, illustration, etc. Object name is scipharm-2012-80-329f5.jpg

UHPLC-ToF MS+ of DP-I.

 

 

The impurity obtained as pale white crystals. mp 71–73. 

RP-UHPLC, tR = 1.8 min (98.5% purity).


MS (ESI, 70 eV): [M + H+] m/z 244. 


FT-IR (KBr), v, cm−1 3371, 3319, 3279, 3173, 3005, 2808, 1696, 1678, 1588, 1406, 1388, 1338, 1305, 1264, 1135, 1067, 873, 790, 680, 569, 485.


1H NMR (400 MHz, DMSO-d6 +D2O, TMS): δ 7.2 (s, 2H, H-7,8), 3.1–3.4 (m, 6H, H-11,13,14 & 16),2.3 (m, 1H, H-12), 2.0 (d, 1H, 11.2 Hz, H-12).


13C NMR (100 MHz, DMSO-d6, TMS): δ 173.8 (C-2,3), 155.1 (C-5,6), 137.6 (C-9,10), 125.1 (C-7,8), 38.8 (C-11), 37.9 (C-12), 38.8 (C-13), 45.8 (C-14), 48.6 (C-16).


UHPLC ToF MS+: m/z [M + H+].Calcd for C13H13N3O2: 244.1086; found: 244.1082.

 

Based on the above spectral data, the molecular formula of DP-I is C13H13N3O2 and the corresponding structure was characterized as 4,6,7,8,9,10-hexahydro-1H-6,10-methanopyrazino[2,3-h][3]benzazepine-2,3-dione.

PMC full text:

Published online 2012 Mar 20. doi:  10.3797/scipharm.1201-08

http://dx.doi.org/10.3797/scipharm.1201-08

 

An external file that holds a picture, illustration, etc. Object name is scipharm-2012-80-329f2.jpg

 

 

 

Chemical structures of Varenicline Tartrate and degradant product (DP-I).........4,6,7,8,9,10-hexahydro-1H-6,10-methanopyrazino[2,3-h][3]benzazepine-2,3-dione.

An external file that holds a picture, illustration, etc. Object name is scipharm-2012-80-329f4.jpg

(A) 1H NMR spectrum of DP-I. (B) Proton decoupled 13C NMR spectrum of DP-I.

 

An external file that holds a picture, illustration, etc. Object name is scipharm-2012-80-329f5.jpg

UHPLC-ToF MS+ of DP-I.

 

 

The impurity obtained as pale white crystals. mp 71–73. 

RP-UHPLC, tR = 1.8 min (98.5% purity).


MS (ESI, 70 eV): [M + H+] m/z 244. 


FT-IR (KBr), v, cm−1 3371, 3319, 3279, 3173, 3005, 2808, 1696, 1678, 1588, 1406, 1388, 1338, 1305, 1264, 1135, 1067, 873, 790, 680, 569, 485.


1H NMR (400 MHz, DMSO-d6 +D2O, TMS): δ 7.2 (s, 2H, H-7,8), 3.1–3.4 (m, 6H, H-11,13,14 & 16),2.3 (m, 1H, H-12), 2.0 (d, 1H, 11.2 Hz, H-12).


13C NMR (100 MHz, DMSO-d6, TMS): δ 173.8 (C-2,3), 155.1 (C-5,6), 137.6 (C-9,10), 125.1 (C-7,8), 38.8 (C-11), 37.9 (C-12), 38.8 (C-13), 45.8 (C-14), 48.6 (C-16).


UHPLC ToF MS+: m/z [M + H+].Calcd for C13H13N3O2: 244.1086; found: 244.1082.

 

Based on the above spectral data, the molecular formula of DP-I is C13H13N3O2 and the corresponding structure was characterized as 4,6,7,8,9,10-hexahydro-1H-6,10-methanopyrazino[2,3-h][3]benzazepine-2,3-dione.

PMC full text:

Published online 2012 Mar 20. doi:  10.3797/scipharm.1201-08

http://dx.doi.org/10.3797/scipharm.1201-08

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