ChemicalBook > Product Catalog >Pharmaceutical intermediates >Heterocyclic compound >Pyridine compound >Ethylpyridine >3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Structure
CAS No.
130049-82-0
Chemical Name:
3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one
Synonyms
3-(2-CHLOROETHYL)-9-HYDROXY-2-METHYL-6,7,8,9-TETRAHYDRO-4H-PYRIDO[1,2-A]PYRIMIDIN-4-ONE;3-(2-ChL;Paliperidone-8;Paliperidone Int 1;Paliperidone USP RC C;3-(2-Chloroethyl)-6,7;Paliperidone IMpurity N;Paliperidone Impurity 55;Paliperidone Impurities105;Paliperidone Intermediate 1
CBNumber:
CB41175684
Molecular Formula:
C11H15ClN2O2
Molecular Weight:
242.7
MOL File:
130049-82-0.mol
Modify Date:
2024/1/9 10:39:30

3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Properties

Melting point 100-102°C
Boiling point 389.3±52.0 °C(Predicted)
Density 1.41±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
solubility Methanol (Slightly)
form Solid
pka 12.97±0.60(Predicted)
color Pale Orange to Yellow
InChI InChI=1S/C11H15ClN2O2/c1-7-8(4-5-12)11(16)14-6-2-3-9(15)10(14)13-7/h9,15H,2-6H2,1H3
InChIKey JKVUGXRJSYRXFN-UHFFFAOYSA-N
SMILES C12C(O)CCCN1C(=O)C(CCCl)=C(C)N=2
CAS DataBase Reference 130049-82-0(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H332-H302
Precautionary statements  P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312
HS Code  2934990002

3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Chemical Properties,Uses,Production

Chemical Properties

Pale-Yellow Solid

Synthesis

A suspension of methanol and 3-(2-Chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2a]pyrimidin-4-one Hydrochloride in a reactor was heated to 50–55 ℃ to achieve dissolution. Charcoal was then added to the solution, and heating was continued. The contents were filtered, and the charcoal cake was washed with methanol. The combined filtrate, the catalyst (10% Pd/C, 50% wet), and dichloromethane were added to a hydrogenation reactor, and the mixture was hydrogenated. The hydrogen pressure was then reduced to 28–43 psi until the completion of the reaction by HPLC. Then, the catalyst was filtered off and washed with methanol. The combined filtrate was evaporated at a temperature below 50 ℃ under reduced pressure to give a dark grayish oil (crude production 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one).

References

[1] Pavankumar V. Solanki . “Preparation of 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, a Key Intermediate for the Synthesis of Paliperidone.” Organic Preparations and Procedures International 48 3 (2016): Pages 296-302.

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3-(2-Chloroethyl)-2-methyl-9-hydroxy-6,7,8,9-tetrahydro-4H-pyrido [1,2-a] pyrimidin-4-one 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-α]pyrimidin-4-one 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4h-pyrido[1,2-a]pyrimidin-4-one ,98% Paliperidone Intermediate 1 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one 9-tetrahydro-9-hydroxy-2-Methyl- 9-Hydroxy-3-(2-chloroethyl)-2-Methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyriMidin-4-one 3-(2-chloroethyl)-9-hydroxy-2-Methyl-4H,6H,7H,8H,9H-pyrido[1,2-a]pyriMidin-4-one 4H-Pyrido[1,2-a]pyriMidin-4-one,3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-Methyl- 3-(2-CHLOROEETHYL)-6,7,8,9-TETRAHYDRO-9-HYDROXY-2-METHYL-4H-PYRIDO (1,2-A) PYRIMIDIN-4-ONE Paliperidone Chloro IMpurity (USP RelatedCoMpound C) Paliperidone USP RC C Paliperidone IMpurity N Paliperidone Related CoMpound C Paliperidone Int 1 Paliperidone Related Compound C (20 mg) (3-(2-Chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-alpha]pyrimidin-4-one) -(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 3-(2-Chloroethyl)-9-hydroxy-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Paliperidone Related Compound C (3-(2-Chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-alpha]pyrimidin-4-one) 3-(2-Chloroethyl)-6,7 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-p Paliperidone Impurity 9(Paliperidone USP RC C) Paliperidone USP Related Compound C Paliperidone-8 3-(2-chloroethyl)-9-hydroxy-2-methyl- )-6,7,8,9-tetrahydro-9-hydroxy-2-methyL 3-(2-ChL -4H-pyrido[1,2-a]pyrimidine-4-one 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrimidin-4-one 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one ISO 9001:2015 REACH Paliperidone Related Compound C (Paliperidone Chloroethyl Impurity) Paliperidone Impurities105 "3-(2-Chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido-[1,2-a] pyrimidine-4-one" 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 130049-82-0 Paliperidone Related Compound C (3-(2-Chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[ (1491831) 3-(2-CHLOROETHYL)-9-HYDROXY-2-METHYL-6,7,8,9-TETRAHYDRO-4H-PYRIDO[1,2-A]PYRIMIDIN-4-ONE Paliperidone Impurity 55 3-(2-Chloroethy)-6,7,8,9- Tetrahydro-2-methyl-4H- pyrido-(1,2-a) pyrimidine-4- one, Hydrochloride 3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-on 130049-82-0 C11H15O2N2Cl Heterocyclic Compounds Bases & Related Reagents Heterocycles Nucleotides