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Friday 1 July 2016

Metoprolol tartrate,





Metoprolol tartrate


Molecular Weight (MW)
684.81
Formula 2C15H25NO3.C4H6O6
CAS No. 56392-17-7


View 
 COA  
NMR 
 HPLC  
Datasheet  
MSDS


 http://repository.ias.ac.in/11453/1/11453.pdf


2-Chloro-1-(4-hydroxyphenyI)ethanone  (2)  separated  out  and  was  filtered.  The  solid  was   crystallized   from  methanol.  Yield  8.52  g  (50%),  rn.p.  151"  (lit. 5m.p.151-152").1R:(KBr)1655crn-l.
'H  NMR  (CDC13)  :  6  4.58  (s,  2H);  6.8  (d,  2H,  J  =  9  Hz);  7.72  (d,  2H,  J  =  9  Hz).  MS  :  Mi  120.5.

2-methoxy-l-(4-hydroxyphenyl)ethanone  (3)  (2.98  g,  90%)  as  white  solid.  m.p.  133-135".  IR  :  (KBr)  3300,   1660  cm-l.  'H  NMR  (CDC13)  :  6  3.4  (s,  3H);  4.55  (s,  2H);  6.8  (d,  ZH,  J  =  9  Hz);  7.75  (d,  2H,  J  =  9  Hz);  9.6  (bs,  lH,  -OH).  MS  :  M+  166.  Analysis  calculated  for  CqHI0O3  :  C,  65.05;  H,  6.07.  Found  :  C,  64.88;  H,  6.27%.

4-(  2-Me thoxyethy1)phenol  (4)  A  solution  of  3  (1.66  g,  10.0  rnmol)  and  10%  paliadium-char-  coal  (86  mg)  in  ethanol  (40  ml)  was  hydrogenated  at  45  psi  for  4  h.  The  solution  was  filtered,  washed   with  ethanol  and   concen-  trated  to  afford  the  crude  product   which  was  distilled  (b.p.  125O/  3  mm)  to  afford  pure  4  (1.46  g,  96%).  IR  :  (film)  3300.   'H  NMR  (CDC13)  :  6  2.84  (t,  2H,  3  =  7  Hz);  3.42  (s,  3H);  3.65  (t,  2H,  J  =  7  Hz);  6.74  (d,  2H,  J  =  9  Hz);  7.1  (d,  ZH,  J  =  9  Hz);  7.0  (br,  1H).  MS:  Mf  152.


 4-(2-Methoxyethyl)phenoxyallyl  ether  (5)  A  rnixture  of  4  (1.52  g,  10.0  mmol),   potassium  carbonate  (1.52  g,  11.0  mmol)  and  ally1  bromide  (1.33  g,  11.0  mrnol)  in  acetone  (25  ml)  was  refluxed  for  7  h.  The  reaction  mixture  fiitered.  Acetone  was  removed  under  reduced  pressure.  The  residue  so  obtained   was  dissolved  in  ethyl  acetate.  The  ethyl  acetate  layer  was  washed  .  with  IN  NaOH  solution,  water,  dried  (Na2S04)  and   concentrated  to  afford  5  (1.63  g,  85%)  a\  colourless  liquid.  'H  NMK  (CDCI3)  :  6  2-81  (t,  2H,  3  =  7  Hz);  3.36  (5,  3H);  3.60  (t,  2H,  J  =  7  Hz);  4.5  (d,  2H);  5.10-5.54  (rn,  2H);    5.77-6.32  (m,  IH);   6.83  (d,  2H,  3  =  9  Hz);  7.13  (d,  2H,  J  =  9  Hz).  MS  :  M+  192.

3[4-(2-Methoxyethy1)phenoxyl-1,Z-propanediol(6)
6  as  d  syrapy  liquid  (1.26  g,  80%).  IK  (nujol)  :  3300  c  in  .  H  NMK  (CDC'13)  -1  1  :  6  2.8  (t,  2H,  3  =  7  Hz);  3.3  (s,  3H);  3.55  (t,  2H,  J  =  7  Hz);  3.62-  4.44  (rn,  5H);  6.81  (d,  2H,  J  =  9  Hz);  7.1  (d,  2H,  J  9  H7).  1Vl5  :  M'  226.

 3-[4-(2-Methoxyethyl)phenoxyl-l,2-epoxypropane(7)
 7  (0.50  g)  as  a  gurrirny  liquid.  'H  NMK  (CDCl,)  :  6  2.74-3.00  (m,  4H);  3.42  (5,  3H);  3.62  (rri,  3H);  3.87-4.04  (111,  2H);  6.9  (d,  2H,  3  9  Hz);  7.2  (d,  2H,  J  =  9  Hz).




 SPECTRAL DATA

 

Metoprolol tartrateIR
 Pharmaceuticals 04 00964f1a 1024




The 1H  Metoprolol tartrate





The  13C NMR spectra Metoprolol tartrate
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 MOM WILL TEACH YOU NMR
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 Amravati Amaralingeswara Swamy Temple

 Amaravati,  Guntur, Andhra Pradesh,  India.

Map of Sri Amareswara Swamy Vari Devasthanam
Amaralingeswara Temple 

Hindu Temple
Amaralingeswara Swamy temple is located in Amararama which is one of the Pancharama Kshetras which is located at Amaravati town near Guntur City in Andhra Pradesh in southern India. Wikipedia
 
 

 
 
 

 

 
 

 

 
 
 

 


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N,N - dibutyladamantane - 1 - carboxamide

N,N-dibutyladamantane-1-carboxamide

Molecular Formula:
C19H33NO
Molecular Weight: 291.47142 g/mol


N,N - dibutyladamantane - 1 - carboxamide (CAS 116415 - 18 - 0)

White solid (12 mg, 14%).  R f =  0.11 ( 2.5% THF in  petroleum ether ).

1 H NMR (400 MHz, CDCl 3 ):  δ 3.33 (t,  J = 7.9 Hz, 4H), 2.03 (s, 3H), 1.99 (s,  6H),  1.77 – 1.64  (m,  6H) ,  1.56 – 1.43  (m,  4H),  1.38 – 1.19  (m,  4H),  0.94  (t,  J =  7.3  Hz,  6H).

 13 C{ 1 H} NMR (100 MHz, CDCl 3 ): δ 176.4, 47.9, 42.1, 39.4, 36.9, 30.7, 28.8, 20.4, 14.1.

EI - MS:  m/z 291.2

 .G M. Dubowchik, L. Padilla, K. Edinger, R. A. Firestone,J. Org. Chem.1996,61, 4676–4684


1 H NMR (400 MHz, CDCl 3 ):  δ 3.33 (t,  J = 7.9 Hz, 4H), 2.03 (s, 3H), 1.99 (s,  6H),  1.77 – 1.64  (m,  6H) ,  1.56 – 1.43  (m,  4H),  1.38 – 1.19  (m,  4H),  0.94  (t,  J =  7.3  Hz,  6H).






13 C{ 1 H} NMR (100 MHz, CDCl 3 ): δ 176.4, 47.9, 42.1, 39.4, 36.9, 30.7, 28.8, 20.4, 14.1.

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Metoprolol lactose adduct

Image for unlabelled figure. Mass spectrometry was performed for this isolated impurity by ESI technique in positive mode. The positive DI-MS spectrum  of isolated impurity exhibited molecular ion peak as [M + H]+ at m/z 592.29 and as sodium adduct [M + Na]+ at m/z 614.28. The MS/MS data displayed a dominant fragment at m/z 574.28 which is 17 amu less than the molecular ion peak indicating a removal of the hydroxyl group.
This indicates that the impurity is Metoprolol-lactose adduct as proposed. The high resolution mass proposed
the probable molecular formula C27H45NO13.

MS and MS/MS spectra of impurity.
The 1H NMR spectrum of this impurity displayed signals at δ = 1.27–1.30(6H), δ = 2.73–2.76 (2H), δ = 2.95–2.98 (1H), δ = 3.12–3.18(1H), δ = 3.23 (3H), δ = 3.44–3.68(11H), δ = 3.73–3.77(2H), δ = 3.83–3.84(2H), δ = 4.15–4.17(3H), δ = 4.41–4.43(1H), δ = 4.64–4.67 (1H), δ = 6.68–6.90 (2H), δ = 7.15–7.17(2H)
corresponding to 37 protons, indicating the Metoprolol adduct impurity possibility as it contains total 45 protons out of which 8 protons are of hydroxyl groups of lactose.
The 1H and 13C NMR spectra of Metoprolol adduct impurity and Metoprolol tartrate  was compared and significant changes were observed. In 1H NMR spectrum of impurity additional 13 protons in aliphatic region were observed. While in 13C NMR, additional 12 carbon signals can be seen. Methylene carbons C21 and C16 were observed at 60.5 and 61.8 ppm respectively and 10 carbon signals were observed between 68.5 ppm to 103 ppm. These signals
confirmed the presence of both lactose as well as Metoprolol moieties in the impurity.
Further to confirm the exact structure of Metoprolol adduct impurity, the 2D NMR HSQC has also been reviewed (see
Supplementary Fig. S-5). It was observed that the proton in aliphatic region showing doublet at (4.41–4.43) ppm corresponds to C22 which appeared at 103 ppm. This confirms the presence of anomeric carbon of pyranose ring. Also C17 appeared at 95.4 ppm found to be quaternary carbon which confirms the presence of furanose anomeric carbon. Proton corresponding to C20 found to shown multiplet in the region of (4.15–4.17) ppm which confirms that C20 is from furanose ring. Apart from these interactions, carbon signals appeared at 70.7, 72.2, 74.5, 61.8 ppm confirming the arabinosyl moiety.
Based on the above observations it has been confirmed that the impurity is Metoprolol lactose adduct and the ‘glucose moiety’ of lactose present in adduct exists in furanose form




The 1H  Metoprolol tartrate




The  13C NMR spectra Metoprolol tartrate
.

The 1H spectra of Metoprolol adduct impurity

The13C NMR spectra of Metoprolol adduct impurity

 
HSQC spectra of Metoprolol adduct impurity

 

 

 

Identification, synthesis, isolation and characterization of new impurity in metoprolol tartrate tablets

  • Ipca Laboratories Ltd., Chemical Research Division, Kandivali Industrial Estate, Kandivali (W). Mumbai 400067, India
 http://www.sciencedirect.com/science/article/pii/S0731708515301357
buchireddy reguri

Buchireddy Reguri

Executive Vice President, IPCA Laboratories
R. Buchi Reddy




Executive Vice President

Ipca laboratories Ltd
 
 
 Dr. Leena Gupta

Dr. Leena Gupta

Senior Research Executive at IPCA
 

 

Dr.Kishor More

Dy.General Manager at Ipca Laboratories Limited
 
Mukesh Jha.

Mukesh Jha

Ph.D.
Research Executive
Ipca Laboratories, Mumbai · CRD
 


Laki Magar
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