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| | (±)-7-[[(4-fluorophenyl)methyl]amino]-8-methylnonan-1-oic acid Basic information |
| | (±)-7-[[(4-fluorophenyl)methyl]amino]-8-methylnonan-1-oic acid Chemical Properties |
| | (±)-7-[[(4-fluorophenyl)methyl]amino]-8-methylnonan-1-oic acid Usage And Synthesis |
| Originator | Zafuleptine,ZYF Pharm Chemical | | Manufacturing Process | 295 g of cyclohexanone and 261 g of morpholine are dissolved in 800 ml of
benzene. After the whole has been dissolved, 1.5 g of p-toluene sulfonic acid
is added and the mixture is heated under reflux. The water formed is
extracted continuously by azeotropic distillation. After 20 hours reflux, the
remaining solvent is distilled off and the oily residue is recovered. 379 g of
the enamine are so obtained, boiling at 115°C to 117°C/2mm. The yield
amounts to 76%. The pure 1-morpholinocyclohex-1-ene has a refractive index
of n D 22 =1.5122.
To solution of 16.7 g 1-morpholinocyclohex-1-ene in 45 ml chloroform, 10.1 g
of triethylamine are added. Over a period of one hour a solution of 1 mole-
equivalent of isobutyroyl chloride in 15 ml chloroform is added, with stirring.
The mixture is stirred for two hours at room temperature and is thereafter
heated at 60°C for 3 hours. It is kept aside for a night, then 150 ml
hydrochloric acid are added. The mixture is shaken and is then allowed to
settle. The chloroformic phase is discarded. The aqueous phase is partially
neutralized with sodium carbonate until the pH value reaches 6 and is then
extracted with chloroform three times. The organic phases are united, washed
with water, dried over sodium sulfate, filtered and evaporated to dryness. The
crude residue is purified by distillation under reduced pressure to give 2-
(isobutyroyl)cyclohexanone.
1 mole-equivalent of 2-(isobutyroyl)cyclohexanone is added to 70 ml of a 5%
aqueous solution of sodium hydroxide. The mixture is heated under reflux for
2 hours. The aqueous solution is then made acidic with a 4 N solution of
hydrochloric acid and is extracted with ether. The ethereous phase is
separated, is washed with a saturated solution of sodium chloride, is dried on
sodium sulfate, is filtered and is evaporated to dryness. The solid residue is
left to stand at room temperature. The crystallization begins quickly. The
crystals are recovered and are recrystallized from n-pentane to give 7-oxo-8-
methylnonanoic acid.
A fresh solution of 1 mole-equivalent of p-fluorobenzylamine and 1 mole
equivalent methylamine is added to a solution of 1 mole-equivalent 7-oxo-8-
methylnonanoic acid in 20 ml ethanol. The mixture is warmed at 40°C for a
night. 0.1 g of platinum oxide is then added and the mixture is hydrogenated
under ordinary pressure at 40°C. After the theoretical amount of hydrogen
has been absorbed, the catalyst is filtered off and the solvent is evaporated
under reduced pressure. The oily residue crystallized quickly, at room
temperature. The product is purified by recrystallizing it from ethyl acetate
and is dried over phosphoric anhydride in a closed vessel. (+/-)-7-((p-
Fluorobenzyl)amino)-8-methylnonanoic acid is a crystalline solid; MP: 88°-
89°C. | | Therapeutic Function | Antidepressant |
| | (±)-7-[[(4-fluorophenyl)methyl]amino]-8-methylnonan-1-oic acid Preparation Products And Raw materials |
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