29216-28-2 Usage
Chemical Properties
White Solid
Originator
Primalan,Berk,UK,1976
Uses
It is an antihistamine
Manufacturing Process
30 g of phenothiazine were added, all at once, to a suspension of 6 g of sodium amide in 240 ml of anhydrous xylene. The mixture was agitated and heated to reflux. When evolution of ammonia ceased (5 hours), 15 g of 3- chloromethyl-quinuclidine hydrochloride were added portionwise over a period of 50 minutes and reflux was then maintained for 22 hours. After cooling to room temperature, 250 ml of distilled water and 250 ml of ethyl acetate were added to the reaction mixture. The aqueous phase was decanted and extracted twice with a total of 250 ml of methyl acetate. The combined organic extracts were extracted three times with a total of 750 ml of a 10% aqueous solution of tartaric acid. The combined acid solutions were treated with 5 g of animal charcoal, filtered and rendered alkaline on an ice bath with 96 ml of 10 N aqueous caustic soda. The oil which separated was extracted three times with a total of 1.500 ml of ethyl acetate. The combined organic extracts were washed to neutrality by washing twice with a total of 1 liter of distilled water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure on a water bath at 45°C. 17 g of oil were obtained which was purified by chromatography on an inert alumina column. 13.3 g of crystallized product were obtained. 10-(3-Quinuclidinyl-methyl)-phenothiazine having a MP of 130°C to 131°C was obtained by recrystallization in boiling acetonitrile. The 3-chloromethyl-quinuclidine hydrochloride used as starting material in this process can be obtained as described by Grob and coll., Helv. Chim. Acta, 37 (1954),1689.
Therapeutic Function
Antihistaminic
Check Digit Verification of cas no
The CAS Registry Mumber 29216-28-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,2,1 and 6 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 29216-28:
(7*2)+(6*9)+(5*2)+(4*1)+(3*6)+(2*2)+(1*8)=112
112 % 10 = 2
So 29216-28-2 is a valid CAS Registry Number.
InChI:InChI=1/C20H22N2S/c1-3-7-19-17(5-1)22(18-6-2-4-8-20(18)23-19)14-16-13-21-11-9-15(16)10-12-21/h1-8,15-16H,9-14H2
29216-28-2Relevant articles and documents
Expedient synthesis of mequitazine an antihistaminic drug by palladium catalyzed allylic alkylation of sodium phenothiazinate
Gonnot, Vanessa,Nicolas, Marc,Mioskowski, Charles,Baati, Rachid
, p. 1300 - 1302 (2009)
A short and straightforward synthesis of the antihistaminic drug mequitazine is reported, based on an efficient palladium catalyzed allylic alkylation of 1-aza-bicyclo[2.2.2]oct-2-en-3-ylmethyl acetate using sodium phenothiazinate in mild conditions.
NOVEL QUINUCLIDINE DERIVATIVE USEFUL IN THE PREPARATION OF MEQUITAZINE
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Page/Page column 3, (2010/05/13)
The invention relates to a 1-aza-bicyclo[2.2.2]oct-2-en-3-ylmethyl acetate of the formula (I), wherein said compound is useful as a synthesis intermediate for the production of mequitazine.
Phenothiazine derivative
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, (2008/06/13)
Phenothiazine derivatives are described of the formula SPC1 In which X1 and X2, which may be the same or different, are H, R, F, Cl, Br, OR, CN, --COR, CH3, --S--R, --SOR, --SO2 R or --SO2 N(CH3)2, where R is an alkyl group having from 1 to 4 carbon atoms, and the quinuclidine ring is substituted by the group --(CH2)x -- in the 2- or 3- position, x being 1 or 2 when said group is substituted in the 2-position and being 0 or 1 when said group is substituted in the 3-position (because of electronic hindrance), and their acid addition and quaternary ammonium salts, have valuable pharmacological properties. In particular, these compounds have anti-histaminic, anti-cholinergic, adrenolytic, neuro-sedative, tranquillizing and/or spasmolytic properties. These compounds are prepared by condensing an appropriate phenothiazine with a quinuclidine derivative of the formula SPC2 In which x has the above-stated meaning and Z is a halogen atom or a reactive ester group.
