Isopropanol → n-Ethyl-2-methyl-decahydroquinolinium hydroiodide

N-Ethyl-2-methyldecahydroquinolinium hydroiodide was prepared according to the method described below. To a solution 100 gm (0.65 mol) of 2-methyldecahydroquinoline (trans and cis) in 350 ml acetonitrile, 111 gm (0.72 mole) of ethyl iodide was added. The mixture was stirred (using an overhead stirrer) at room temperature for 96 hours. Then, an additional ½ mole equivalent of ethyl iodide was added and the mixture was heated at reflux for 6 hours. The reaction mixture was concentrated on a rotary evaporator at reduced pressure and the obtained solids were rinsed with 500 ml ethyl ether to remove any unreactive amines and excess iodide. The reaction afforded a mixture of two N-ethyl-2-methyl-decahydroquinolinium hydroiodide salts (mono-ethyl derivatives) and a small mixture of the quaternized derivatives. The products were isolated by recrystallization from isopropyl alcohol several times to give the pure trans-fused ring N-ethyl-2-methyl-decahydroquinolinium hydroiodide and the pure cis-fused ring N-ethyl-2-methyl-decahydroquinolinium hydroiodide (see the scheme below).

1. customN-Ethyl-2-methyldecahydroquinolinium hydroiodide was prepared
2. temperaturethe mixture was heated
3. temperatureat reflux for 6 hours
4. concentrationThe reaction mixture was concentrated on a rotary evaporator at reduced pressure
5. washthe obtained solids were rinsed with 500 ml ethyl ether
6. customto remove any unreactive amines and excess iodide
7. customThe reaction afforded
8. additiona small mixture of the quaternized derivatives

ORD record

ord-b36369de3d69446d83bfd5a1a127fcc9

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07226569B2