4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide
- CAS No.
- 364-62-5
- Chemical Name:
- 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide
- Synonyms
- Metoclopramide;DEL;Metaclopramide;Primperan;Metochlopramide;C07868;Parmid;Plasil;del1267;DEL 1267
- CBNumber:
- CB4506227
- Molecular Formula:
- C14H22ClN3O2
- Molecular Weight:
- 299.8
- MDL Number:
- MFCD00211338
- MOL File:
- 364-62-5.mol
| Melting point | 146-148°C |
|---|---|
| Boiling point | 418.7±45.0 °C(Predicted) |
| Density | 1.2432 (rough estimate) |
| refractive index | 1.5200 (estimate) |
| storage temp. | 2-8°C |
| solubility | Practically insoluble in water, sparingly soluble or slightly soluble in ethanol (96 per cent), slightly soluble in methylene chloride |
| pka | pKa 0.42± 0.03;9.71± 0.02(H2O)(Approximate) |
| color | White to Off-White |
| BRN | 1884366 |
| CAS DataBase Reference | 364-62-5(CAS DataBase Reference) |
| FDA UNII | L4YEB44I46 |
| NCI Dictionary of Cancer Terms | metoclopramide |
| ATC code | A03FA01 |
| NIST Chemistry Reference | Benzamide, 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-methoxy-(364-62-5) |
4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide price More Price(20)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | M1824990 | Metoclopramide European Pharmacopoeia (EP) Reference Standard | 364-62-5 | m1824990 | $220 | 2024-03-01 | Buy |
| Sigma-Aldrich | 32473 | Metoclopramide VETRANAL | 364-62-5 | 100mg | $140 | 2024-03-01 | Buy |
| TRC | M338698 | Metoclopramide | 364-62-5 | 1g | $65 | 2021-12-16 | Buy |
| AK Scientific | H780 | Metoclopramide | 364-62-5 | 100mg | $72 | 2021-12-16 | Buy |
| AK Scientific | H780 | Metoclopramide | 364-62-5 | 1g | $144 | 2021-12-16 | Buy |
4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Chemical Properties,Uses,Production
Uses
Metoclopramide is a treatment of choice of post-operative nausea and vomiting (PONV) prophylaxis.
Chemical Properties
White or almost white, fine powder.
Originator
Primperan,Delagrange,France,1964
Uses
Metoclopramide is a treatment of choice of post-operative nausea and vomiting (PONV) prophylaxis.
Uses
antidiabetic
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.
4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Changzhou Rokechem Technology Co., Ltd. | 18758118018 | sales001@rokechem.com | China | 255 | 58 |
| shandong perfect biotechnology co.ltd | +86-53169958659; +8618596095638 | sales@sdperfect.com | China | 294 | 58 |
| Guangzhou Tengyue Chemical Co., Ltd. | +86-86-18148706580 +8618826483838 | evan@tyvovo.com | China | 152 | 58 |
| Hebei Xinsheng New Material Technology Co., LTD. | +86-16632316109 | xinshengkeji@xsmaterial.com | China | 1100 | 58 |
| Shanghai Daken Advanced Materials Co.,Ltd | +86-371-66670886 | info@dakenam.com | China | 15928 | 58 |
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 32480 | 60 |
| career henan chemical co | +86-0371-86658258 | sales@coreychem.com | China | 29914 | 58 |
| Jinan Jianfeng Chemical Co., Ltd | 0531-88110457; +8615562555968 | info@pharmachemm.com | China | 222 | 58 |
| Hubei Jusheng Technology Co.,Ltd. | 18871490254 | linda@hubeijusheng.com | CHINA | 28180 | 58 |
| Chongqing Chemdad Co., Ltd | +86-023-61398051 +8613650506873 | sales@chemdad.com | China | 39916 | 58 |
View Lastest Price from 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-03-28 | Metoclopramide
364-62-5
|
US $0.00 / kg | 25kg | 98% | Inquiry | PNP Biotech Co. Ltd | |
 |
2024-03-12 | metoclopramide
364-62-5
|
US $0.00 / g | 1g | 98% HPLC | 1ks | shandong perfect biotechnology co.ltd | |
 |
2023-12-20 | Metoclopramide, 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide
364-62-5
|
US $90.00 / kg | 1kg | 99% Purity (What/sapp: +86 18145728414) | 1000 Tons/Month | Guangzhou Tengyue Chemical Co., Ltd. |
-
- Metoclopramide
364-62-5
- US $0.00 / kg
- 98%
- PNP Biotech Co. Ltd
-
- metoclopramide
364-62-5
- US $0.00 / g
- 98% HPLC
- shandong perfect biotechnology co.ltd
-
- Metoclopramide, 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide
364-62-5
- US $90.00 / kg
- 99% Purity (What/sapp: +86 18145728414)
- Guangzhou Tengyue Chemical Co., Ltd.