Réaction #46138

Équation de réaction

1,5-dibromopentane

1,5-dibromopentane

3-(2-aminoethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one hydrochloride

triethylamine

→

HCl

6-Methoxy-2-methyl-4-phenyl-3-(2-piperidin-1-ylethyl)isoquinolin-1(2H)-one hydrochloride

Solvants

2-methyl-2-propanol

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling to room temperature
2. 2
   Concentrationthe mixture was concentrated in vacuo
3. 3
   AutreThe crude residue was purified by preparative reversed phase HPLC
4. 4
   ConcentrationThe pure fractions were concentrated in vacuo
5. 5
   Lavagewashed with saturated NaHCO3 solution and brine
6. 6
   Séchagedried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo
9. 9
   workup.ADDITIONtreated with excess ethereal HCl
10. 10
    Concentrationconcentrated in vacuo

Mode opératoire

To a solution of 3-(2-aminoethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one hydrochloride (100 mg, 0.290 mmol) in 15 mL of 2-methyl-2-propanol in a pressure tube was added triethylamine (0.142 mL, 1.02 mmol), followed by 1,5-dibromopentane (0.047 mL, 0.348 mmol). The mixture was heated at 150° C. overnight. Another portion of 1,5-dibromopentane was added (0.023 mL), and the heating continued for another 24 hours. After cooling to room temperature, the mixture was concentrated in vacuo. The crude residue was purified by preparative reversed phase HPLC. The pure fractions were concentrated in vacuo, taken up in EtOAc and washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The product was taken up in dichloromethane, treated with excess ethereal HCl, and concentrated in vacuo to provide the HCl salt. Proton NMR for the product was consistent with the titled compound. ESI+MS: 377.19 [M+H]+.

Source