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

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.

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


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:

Sci Pharm. 2012 Apr-Jun; 80(2): 329–336. Published online 2012 Mar 20. doi:  10.3797/scipharm.1201-08

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

9,10-Dihydro-9,10-ethanoanthracene-11,12-trans-dicarboxylic acid diethyl ester

9,10-Dihydro-9,10-ethanoanthracene-11,12-trans-dicarboxylic acid diethyl ester

Name	9,10-Dihydro-9,10-ethanoanthracene-11,12-trans-dicarboxylic acid diethyl ester
Synonyms
Name in Chemical Abstracts	9,10-Ethanoanthracene-11,12-dicarboxylic acid, diethyl ester, trans-
CAS No	93368-53-7
EINECS No
Molecular formula	C22H22O4
Molecular mass	350.42
SMILES code	c1cccc2[C@@H]3[C@H](C(=O)OCC)[C@@H](C(=O)OCC)[C@H](c12)c4ccccc43

1H NMR

1H-NMR: 9,10-Dihydro-9,10-ethanoanthracene-11,12-trans-dicarboxylic acid diethyl ester
250 MHz, CDCl3
delta [ppm]	mult.	atoms	assignment
1.23	t (3J = 7.2 Hz)	6 H	CH3 ethyl
3.45	m	2 H	11-H, 12-H (-CH-COO-)
4.08	m	4 H	CH2 ethyl
4.75	m	2 H	9-H, 10-H

13C-NMR

13C-NMR: 9,10-Dihydro-9,10-ethanoanthracene-11,12-trans-dicarboxylic acid diethyl ester
62.5 MHz, CDCl3
delta [ppm]	assignment
14.2	CH3 (ethyl ester)
46.7	C9, C10 (CH)
47.7	C11, C12 (CH-COO)
60.9	CH2 (ethyl ester)
123.8	CH arom.
124.5	CH arom.
126.2	CH arom.
126.3	CH arom.
140.3	C quart. arom.
142.0	C quart. arom.
172.3	C(=O)O-
76.5-77.5	CDCl3

IR

IR: 9,10-Dihydro-9,10-ethanoanthracene-11,12-trans-dicarboxylic acid diethyl ester
[KBr, T%, cm-1]
[cm-1]	assignment
3074, 3026	arom. C-H valence
2981	aliph. C-H valence
2935, 2897	aliph. C-H valence
1739	C=O valence, ester
1467	arom. C=C valence

+

; Side reactions

Synthesis of 9,10-dihydro-9,10-ethanoanthracene-11,12-trans-dicarboxylic acid diethyl ester

Reaction type:	cycloaddition, Diels-Alder reaction
Substance classes:	alkene, aromatics, carboxylic acid ester, diene, dienophile, acid catalyst
Techniques:	working with moisture exclusion, heating under reflux, stirring with magnetic stir bar, filtering, evaporating with rotary evaporator, recrystallizing, use of an ice cooling bath, heating with oil bath

Equipment

Batch scale:

0.01 mol

0.1 mol

Anthracene

	three-necked flask 1000 mL			adapter with ground-glass joint and hose coupling
	protective gas piping			reflux condenser
	drying tube			bubble counter
	powder funnel			heatable magnetic stirrer with magnetic stir bar
	rotary evaporator			ice bath
	exsiccator with drying agent			oil bath

Operating scheme

MULTAN, PAKISTAN



Mutlan is an important city of Pakistan which is also known as the city of Saints. The history of Multan begins with the Alexander and later on Kushans, Arabs, Huns, Ghaznavi, Afghans, Mongols, Sikhs, Mughals and British ruled over the city. It is the city of Sufis and Saints who preached the Islam in this region. In the South Asia Multan is the oldest city.
.

Multan Things to Do

 See all 10 Things to Do in Multan

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  Baha-ud-din Zakariya Mazar

  Sheikh Baha-ud-din Zakariya (1170-1267) was a sufi saint who for several years travelled the region from Baghdad, Iraq to India preaching Islam, and made his final abode in Multan. His offsprings and disciples travelled all over India to preach. His most famous descendant is Shah...  more
  
  
• 

  Shah Rukn-e-Alam's tomb

  Situated on top of a small hillock, behind the old ruins of Multan Fort, the Mazar and its majestic dome is the first landmark visible when you enter proper Multan. Shah Rukn-e-Alam (1251-1335) was a Sufi saint in Multan. He was revered by his followers, and to this date thousands of pilgrims from all over...  more
  
  
• 

  Other Saints and Sufis Mazars

  Multan is known as City of Saints, and this is evident by the number of Masuleums, Mazars, Dargas, or tombs situated in this city. Some of them are listed below.1 Hazrat Baha-ud-Din Zakaria2 Shah Rukn-i-Alam3 Shah Shams Sabzwari4 Shah Gardez5 Musa Pak Shaheed6 Hazrat Hafiz Muhammad...  more
  
  
• 

  Ghanta Ghar (Clock Tower house)

  Ghanta Ghar whch is situated in the city center is the city government head quarter. (not a great picture, taken from a moving car)
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  Multan Fort

  The Multan Fort on a high mound of earth which separated it from the old branch of the river Ravi. There are now only remnant of this old fort, which was considered as one of the best fort (defense wise) built in the sub-continent. The fort was destroyed when the British took over. During its haydays the fort walls were was almost 1.6...  more
  
  
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  King mosque Eid Gah

  This Masjid is a marvelous piece of architecture of multan.it is a very beautiful masjid and must to visit place of Multran city
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  Shrines must to visit

  Given below is list of must to visit shrines in Multan1.Shrine B.B Pak Damman2.Shrine Hameed-ud-Din Hakim3.Shrine Qutab-al-quteeb'Moj Daryan'4.Shrine-Syed Pir Sakhi Shah Hasan Prwana5.Shrine-Qazi Qutab-ud-Din Kashani6.Shrine-Syed Hasan Kanjzee7.Shrine-Hazarat Shah Dana Shaheed8.Shrine-Abu...  more
  
  
• 

  Shrines of the sufi hermits

  Hi Awais,All the destinations in Pakistan, they've their own attraction or somethijng very special in that area, likewise in Hunza, you can't find the shrines of the sufi hermits, or in Multan, the mountains like Nanga parbat or Kalash tribes in Lahore?Multan, Medina-tul-awlia, the city of saints, famous all over the...  more
  
  
• 

  Visiting Historical Places

  As I describe before that Multan is the city of Saints so there r so many Tombs to Visit and explore the history.
   more
  
  

 Multan Hotels

• 

  Ramada Multan

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