ChemicalBook CAS DataBase List Rasagiline mesylate

Rasagiline mesylate synthesis

9synthesis methods

Product Name:Rasagiline mesylate
CAS Number:161735-79-1
Molecular formula:C13H17NO3S
Molecular Weight:267.344

1-Indanone (122) was condensed with benzyl amine to give corresponding enamine which was reduced with sodium borohydride in ethanol to give racemic Nbenzyl- 1-inda-namine (123) in 82% yield. The racemic benzylamine 123 was resolved with L-tartaric acid and recrystallized from boiling water to give optical pure Rbenzylamine 124 as a tartarate salt. The recovered S-isomer 125 can be racemized under basic condition to give back as the starting racemic 123. Compound 124 was hydrogenated and basified to give free amine 126 in 72 % yield which was alkylated with propargyl chloride and K2CO3 in hot acetonitrile to yield free resagiline. Finally resagiline mesilate (XVII) was obtained by treating resagiline with methanesulfonic acid in refluxing IPA.

75-75-2 Synthesis

75-75-2
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136236-51-6 Synthesis

136236-51-6
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161735-79-1
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Yield:161735-79-1 98%

Reaction Conditions:

in isopropyl alcohol; for 1 h;Reflux;

Steps:

2.10. Synthesis of (R)-rasagiline mesylate (R-7)

A suspension of (R)-N-propargyl-1-aminoindan (R-6) (50 mg,0.29 mmol) in 5 mL of isopropanol and 3 L of methanesulfonic acidwas heated to reflux for 1 h. After, the mixture was allowed to coolto 5C. The obtained suspension was filtered, and the collected solidwas washed with 1.5 mL of isopropanol, affording the correspond-ing optically active (R)-rasagiline mesylate (R-7) as a white solid in98% yield.

References:

De Mattos, Marcos Carlos;De Fonseca, Thiago Sousa;Da Silva, Marcos Reinaldo;De Oliveira, Maria Da Concei??o Ferreira;De Lemos, Telma Leda Gomes;De Marques, Ricardo Araújo [Applied Catalysis A: General,2015,vol. 492,# 1,p. 76 - 82]

75-75-2 Synthesis

75-75-2
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