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| | 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Basic information |
| Product Name: | 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one | | Synonyms: | 3-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]-pyrididine-4-one (intermediate of Risperidone);3-(2-CHLOROETHYL)-2-METHYL-6,7,8,9-TETRAHYDRO-4H-PYRIDO[1,2-A]PYRIMIDIN-4-ONE;3-(2-CHLORO-ETHYL)-2-METHYL-6,7,8,9-TETRAHYDRO-PYRIDO[1,2-A]PYRIMIDIN-4-ONE;3-(2-CHLOROETHYL)-6,7,8,9-TETRAHYDRO-2-METHYL-4H-PYRIDINO[1,2-A]PYRIMIDINE-4-ONE;3-(2-CHLOROETHYL)-6,7,8,9-TETRAHYDRO-2-METHYL-4H-PYRIDO(1,2A)PYRIMIDINE-4-ONE;3-(2-CHLOROETHYL)-6,7,8,9-TETRAHYDRO-2-METHYL-4H-PYRLDO[1,2-A]PYRIMDIN-4-ONE;3-2(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-alpha]pyrimnidin-4-one;3-2(2-CHLOROETHYL)-6,7,8,9-TETRAHYDRO-2-METHYL-4H-PYRIDO[1,2-A]PYRIMDIN-4-ONE | | CAS: | 63234-80-0 | | MF: | C11H15ClN2O | | MW: | 226.7 | | EINECS: | 613-192-1 | | Product Categories: | Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Intermediates;Nucleotides and Nucleosides;(intermediate of Risperidone) | | Mol File: | 63234-80-0.mol | ![3-(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Structure](CAS/GIF/63234-80-0.gif) |
| | 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Chemical Properties |
| Melting point | 68.5-69.5 °C | | Boiling point | 337 °C | | density | 1.30 | | Fp | 157 °C | | storage temp. | Sealed in dry,Room Temperature | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Solid | | pka | 3.58±0.70(Predicted) | | color | White to Off-White | | InChI | InChI=1S/C11H15ClN2O/c1-8-9(5-6-12)11(15)14-7-3-2-4-10(14)13-8/h2-7H2,1H3 | | InChIKey | CMWCQQUYLPYOMY-UHFFFAOYSA-N | | SMILES | C12CCCCN1C(=O)C(CCCl)=C(C)N=2 | | CAS DataBase Reference | 63234-80-0(CAS DataBase Reference) |
| Hazard Codes | T | | Risk Statements | 25 | | Safety Statements | 45 | | RIDADR | UN3261 | | HS Code | 2933.99.9701 | | HazardClass | IRRITANT |
| | 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Usage And Synthesis |
| Chemical Properties | White Solid | | Uses | 3-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (Risperidone EP Impurity L) is an intermediate in the synthesis of Risperidone (R525000), which is a combined serotonin (5-HT2) and dopamine (D2) receptor antagonist. | | Synthesis | The general procedure for the synthesis of 3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one from 3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one is as follows: 28 g of 3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one obtained in step A) was dissolved in 90 mL 6N hydrochloric acid. -a]pyrimidin-4-one was dissolved in 90 mL of 6N hydrochloric acid, followed by the addition of 2.8 g of 10% palladium carbon catalyst to the solution. The reaction mixture was subjected to 35 psi hydrogen pressure and hydrogenated at room temperature with stirring for 8 hours. Upon completion of the reaction, the mixture was filtered through diatomaceous earth (Cellite) to remove the catalyst. The filtrate was concentrated under reduced pressure to give a residue. To the residue was added 200 mL of isopropanol and the mixture was stirred. The precipitated solid was collected by filtration and dried to give 25.1 g of the target product 3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one as white crystals in 90% yield. | | References | [1] Patent: WO2004/35573, 2004, A1. Location in patent: Page 9
[2] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[3] Letters in Drug Design and Discovery, 2011, vol. 8, # 10, p. 988 - 995
[4] Medicinal Chemistry, 2013, vol. 9, # 2, p. 240 - 248 |
| | 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Preparation Products And Raw materials |
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