DIMETHINDENE CAS 5636-83-9
Introduction：Basic information about DIMETHINDENE CAS 5636-83-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
DIMETHINDENE Basic information
| Product Name: | DIMETHINDENE |
| Synonyms: | DIMETHINDENE;DIMETINDENE;2-(1-(2-(2-Dimethylaminoethyl)inden-3-yl)ethyl)pyridine;demethindene;Dimethpyrindene;Forhistal;N,N-Dimethyl-2-(3-[1-(2-pyridinyl)ethyl]-1H-inden-2-yl)ethanamine;Pyridine, 2-(1-(2-(2-(dimethylamino)ethyl)inden-3-yl)ethyl)- |
| CAS: | 5636-83-9 |
| MF: | C20H24N2 |
| MW: | 292.42 |
| EINECS: | 227-083-8 |
| Product Categories: | Miscellaneous |
| Mol File: | 5636-83-9.mol |
DIMETHINDENE Chemical Properties
| Melting point | 50 - 53°C |
| Boiling point | 424.35°C (rough estimate) |
| density | 1.0073 (rough estimate) |
| refractive index | 1.5640 (estimate) |
| storage temp. | Refrigerator, under inert atmosphere |
| solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) |
| form | Solid |
| pka | 9.58±0.28(Predicted) |
| color | Pale Brown to Light Brown |
| Water Solubility | 238.6mg/L(37 ºC) |
| InChI | InChI=1S/C20H24N2/c1-15(19-10-6-7-12-21-19)20-17(11-13-22(2)3)14-16-8-4-5-9-18(16)20/h4-10,12,15H,11,13-14H2,1-3H3 |
| InChIKey | MVMQESMQSYOVGV-UHFFFAOYSA-N |
| SMILES | C1C2=C(C=CC=C2)C(C(C2=NC=CC=C2)C)=C1CCN(C)C |
Safety Information
| Originator | Fenistil,Zyma,W. Germany,1961 |
| Definition | ChEBI: Dimetindene is an indene. |
| Manufacturing Process | 26 grams of 2-ethylpyridine is added dropwise with cooling to 20°C and in anatmosphere of nitrogen to a stirred solution of 650 ml of an 0.37 molarsolution of phenyl lithium in benzene. After two hours a solution of 10 gramsof 2-(2-dimethylaminoethyl)-indan-1-one in 50 ml of dry ether is added overa period of five minutes while stirring and cooling to room temperature. Afterstanding for 24 hours the organo-lithium compounds are decomposed by theaddition of 50 ml of water with external cooling. After separating the waterphase from the organic solution, the latter is washed several times with 50 mlof water, and then extracted with a mixture of 40 ml of concentratedhydrochloric acid and 100 ml of water. The acidic solution, containing the 2-(2-dimethylaminoethyl)-1-[1-(2-pyridyl)-ethyl]-indan-1-ol is heated on the steam bath for thirty minutes to effectdehydration to the desired indene derivative. The solution is cooled, madestrongly basic with an aqueous solution of ammonia and then extracted withether. The ether phase is dried over sodium sulfate, filtered, evaporated andthe residue distilled. At 15 mm pressure the excess of 2-ethylpyridine is removed, at 120°C/0.5mm some unreacted 2-(2-dimethylaminoethyl)-indene distills and at 165°-175°C/0.5 mm the 2-(2-dimethylaminoethyl)-3-[1-(2-pyridyl)-ethyl]-indene iscollected. It may be converted to an aqueous solution of the dihydrochlorideby dissolving it in the appropriate amount of dilute hydrochloric acid. To a solution of 1.0 gram of 2-(2-dimethylaminoethyl)-3[1-(2-pyridyl)-ethyl]-indene in 10 ml of ethanol is added while stirring and heating 0.4 gram ofmaleic acid. On cooling the 2-(2-dimethylaminoethyl)-3-[1-(2-pyridyl)-ethyl]-indene maleate crystallizes, is filtered off, washed with a small amount ofethanol and recrystallized from ethanol, MP 158°C. |
| Therapeutic Function | Antihistaminic |
| Synthesis | Benzylmalonic acid is esterifiedwith dihydropyran and reacted with sodiumhydride and 2-dimethylaminoethyl chloride intoluene to give ditetrahydropyranyl-2-benzyl-2-(2-dimethylaminoethyl)malonate, which is cyclizedwith the help of polyphosphoric acidto 2-(2-dimethylaminoethyl)-indan-1-one. Thiscompound reacts with 2-ethylpyridine and phenyllithiumto give the carbinol, which is dehydratedby heating to dimetindene . |
DIMETHINDENE Preparation Products And Raw materials
| Raw materials | 2-[2-(DiMethylaMino)ethyl]-1-indanone-->Phenyllithium-->2-Ethylpyridine-->Maleic acid |
