364-62-5 Usage
Uses
Different sources of media describe the Uses of 364-62-5 differently. You can refer to the following data:
1. Metoclopramide is a treatment of choice of post-operative nausea and vomiting (PONV) prophylaxis.
2. antidiabetic
Originator
Primperan,Delagrange,France,1964
Definition
ChEBI: A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine.
Manufacturing Process
The N-(diethylaminoethyl)-2-methoxy-4-aminobenzamide used as the starting
material may be prepared from o-toluidine. The o-toluidine is initially nitrated
with nitric acid to produce 4-nitro-o-toluidine. The 4-nitro-o-toluidine is then
converted to 2-hydroxy-4-nitrotoluene by heating with nitrous acid. By
reacting the resulting 2-hydroxy-4-nitrotoluene with dimethyl sulfate, 2-
methoxy-4-nitrotoluene is formed. The 2-methoxy-4-nitrotoluene is oxidized
with potassium permanganate to produce 2-methoxy-4-nitrobenzoic acid. The
latter substituted benzoic acid is treated with thionyl chloride to form 2-
methoxy-4-nitrobenzoyl chloride. A methyl ethyl ketone solution of the 2-
methoxy-4-nitrobenzoyl chloride is added over a period of about 1? hours to
a methyl ethyl ketone solution containing an equal molecular quantity of N,Ndiethylethylene diamine while stirring and maintaining the temperature
between 0°C and 5°C. The N-(diethylaminoethyl)-2-methoxy-4-
nitrobenzamide hydrochloride formed precipitates. It is filtered, washed twice
with methyl ethyl ketone, dissolved in alcohol, and reduced catalytically in an
absolute isopropyl alcohol solution to form N-(diethylaminoethyl)-2-methoxy-
4-aminobenzamide. The base is obtained by precipitating with sodium
hydroxide.80 g (0.3mol) of N-(2-diethylaminoethyl)-2-methoxy-4-aminobenzamide are
dissolved in small portions in 150 cc of acetic acid. The mixture is cooled and
45 g (0.45 mol) of acetic anhydride are added, and the solution obtained is
heated for two hours on a water bath. After cooling, the solution is decanted
into a round-bottomed flask with a stirrer, a thermometer and a tube for
introducing the chlorine. It is stirred and the current of chlorine is passed
through, the temperature being maintained between 20°C and 25°C. The
stirring is continued for one hour after the completion of the absorption of the
chlorine.The mixture obtained is poured into 2 liters of water and the base is
precipitated with 30% soda. The precipitated base is extracted with 400 cc of
methylene chloride. After evaporation of the solvent, the N-(2-
diethylaminoethyl)-2-methoxy-4-acetamino-5-chlorobenzamide formed
crystallizes. The melting point is 86°C to 87°C and the yield is 95%.To obtain the corresponding amino derivative, 109 g of base are heated under
agitation in a round-bottomed flask with 300 cc of 35-36% concentrated
hydrochloric acid and 600 cc of water. It is heated on a water bath until
dissolution is complete, then maintained at boiling point for 90 minutes,
cooled, diluted with 1 liter of water, and neutralized with about 350 cc of 30%
soda. The N-(2-diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide
formed crystallizes, is centrifuged and washed in water. Its melting point is
122°C and the yield is 74%.To obtain the corresponding dihydrochloride, the base is dissolved in absolute
alcohol (3 volumes) and to that solution is added 5 N alcoholic hydrochloric
acid. The dihydrochloride precipitates, is centrifuged and washed with alcohol.
It is a solid white material, having a melting point of 134°C to 135°C.
Brand name
Maxolon (King); Reglan (Baxter
Healthcare); Reglan (Robins); Reglan (Schwarz Pharma).
Therapeutic Function
Antiemetic
General Description
Metoclopramide is typically employed as an antiemetic drug or a gastrointestinal prokinetic drug in adults and children.
Check Digit Verification of cas no
The CAS Registry Mumber 364-62-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,6 and 4 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 364-62:
(5*3)+(4*6)+(3*4)+(2*6)+(1*2)=65
65 % 10 = 5
So 364-62-5 is a valid CAS Registry Number.
InChI:InChI=1/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)
364-62-5Relevant articles and documents
New findings in the synthesis of metoclopramide
Pakula,Butkiewicz,Trojanowska,Ruszczak
, p. 297 - 300 (1980)
-
COMPOUND, COMPOSITION AND USES THEREOF
-
Paragraph 00169, (2017/03/28)
The disclosures herein provide compounds of formula I, formula II, formula III, formula IV, formula V, formula VI and formula VII or its pharmaceutical acceptable compositions and salts, as well as polymorphs, enantiomers, stereoisomers, solvates, and hydrates thereof. These compositions or salts may be formulated as pharmaceutical compositions. The pharmaceutical compositions may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of stomach and esophageal problems or its associated complications.
Ex situ generation of stoichiometric and substoichiometric 12CO and 13CO and its efficient incorporation in palladium catalyzed aminocarbonylations
Hermange, Philippe,Lindhardt, Anders T.,Taaning, Rolf H.,Bjerglund, Klaus,Lupp, Daniel,Skrydstrup, Troels
, p. 6061 - 6071 (2011/06/19)
A new technique for the ex situ generation of carbon monoxide (CO) and its efficient incorporation in palladium catalyzed carbonylation reactions was achieved using a simple sealed two-chamber system. The ex situ generation of CO was derived by a palladium catalyzed decarbonylation of tertiary acid chlorides using a catalyst originating from Pd(dba)2 and P(tBu)3. Preliminary studies using pivaloyl chloride as the CO-precursor provided an alternative approach for the aminocarbonylation of 2-pyridyl tosylate derivatives using only 1.5 equiv of CO. Further design of the acid chloride CO-precursor led to the development of a new solid, stable, and easy to handle source of CO for chemical transformations. The synthesis of this CO-precursor also provided an entry point for the late installment of an isotopically carbon-labeled acid chloride for the subsequent release of gaseous [ 13C]CO. In combination with studies aimed toward application of CO as the limiting reagent, this method provided highly efficient palladium catalyzed aminocarbonylations with CO-incorporations up to 96%. The ex situ generated CO and the two-chamber system were tested in the synthesis of several compounds of pharmaceutical interest and all of them were labeled as their [ 13C]carbonyl counterparts in good to excellent yields based on limiting CO. Finally, palladium catalyzed decarbonylation at room temperature also allowed for a successful double carbonylation. This new protocol provides a facile and clean source of gaseous CO, which is safely handled and stored. Furthermore, since the CO is generated ex situ, excellent functional group tolerance is secured in the carbonylation chamber. Finally, CO is only generated and released in minute amounts, hence, eliminating the need for specialized equipment such as CO-detectors and equipment for running high pressure reactions.
