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2-(1,2,3,5,6,7-hexahydropyrrolizin-8-yl)acetonitrile, commonly referred to as HPHPA, is a compound that has been widely used in various chemical reactions and synthesis routes.
It is an important building block in organic chemistry and has been used as a versatile intermediate in the synthesis of various drugs, agrochemicals, and other chemical products.
One of the most common synthetic routes for HPHPA involves the reaction of 3-cyano-2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acid with 2-iodoacetamide in the presence of a polar protic solvent, such as water or methanol.
The reaction is typically carried out in the presence of a Lewis acid catalyst, such as BF3 or AlCl3, and the resulting product is isolated by precipitation with a polar protic solvent, such as ether or pentane.
Another synthetic route for HPHPA involves the reaction of 2-(chloromethyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-7(8H)-one with 2,2,2-trichloro-1,3-oxazolidine-4,6-dione in the presence of a phase transfer catalyst, such as TBAB or TBAAC.
The reaction is typically carried out in an inert organic solvent, such as THF or DMF, and the resulting product is isolated by filtration and washing with a polar solvent, such as water or ethanol.
Yet another synthetic route for HPHPA involves the reaction of 7-iodo-2-(4-nitrophenyl)quinolin-4-amine with 2,2,2-trichloro-1,3-oxazolidine-4,6-dione in the presence of a tertiary amine, such as triethylamine or pyridine.
The reaction is typically carried out in an inert organic solvent, such as THF or DMF, and the resulting product is isolated by filtration and washing with a polar solvent, such as water or ethanol.
HPHPA has been widely used as a versatile intermediate in the synthesis of various drugs and agrochemicals.
For example, HPHPA can be converted to 2-(1,2,3,5,6,7-hexahydro-1H-pyrrolo[2,1-c][1,4]benzoxazepin-8-yl)acetonitrile, which is a potent and selective GABA(B) receptor antagonist.
HPHPA can also be converted to 2-[[2-(1,2,3,5,6,7-hexahydro-1H-pyrrolo[2,1-c][1,4]benzoxazepin-8-yl)acetyl]amino]acetic acid, which is a potent and selective glutamate receptor antagonist.
In addition to its use as an intermediate in drug synthesis, HPHPA has also been used as a building block in the synthesis of agrochemicals.
For example, HPHPA can be converted to 2-(1,2,3,5,6,7-hexahydro-1H-pyrrolo[2,1-c][1,4]benzoxazepin-8-yl)acetonitrile, which is a potent herbicide that can be used to control weeds in crops.
Overall, HPHPA is an important building block in organic chemistry and has a wide range of applications in various chemical reactions and synthesis routes.
Its versatility and utility make it an important compound in the development of new drugs, agrochemicals, and other chemical products.