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Chemical Structure| 1010-26-0 Chemical Structure| 1010-26-0

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Chemical Structure| 1010-26-0

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Product Details of [ 1010-26-0 ]

CAS No. :1010-26-0
Formula : C10H14O3
M.W : 182.22
SMILES Code : O=C(O1)CC2(CCCCC2)CC1=O
MDL No. :MFCD00040292
InChI Key :XNDSIASQMRYFSW-UHFFFAOYSA-N
Pubchem ID :2734289

Safety of [ 1010-26-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1010-26-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1010-26-0 ]

[ 1010-26-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1010-26-0 ]
  • [ 99189-60-3 ]
YieldReaction ConditionsOperation in experiment
Example 1; 3246 kg (3748 1) of toluene and in nitrogen flow and under stirring 1874 kg of 1,1- cyclohexanediacetic acid were charged in a reactor. A dense suspension was obtained. The suspension was heated at 80°C and 1146 kg (1064 1) of acetic anhydride were added thereto in 2-3 hours. The addition was slightly endothermic. During the addition the inner temperature was kept at about 80°C. Upon proceeding with the addition the reaction mixture fluidifie until complete dissolution. The mixture was left under stirring for about 30 min. at about 80°C inside, then it was gradually vacuum-placed and it was distilled by keeping the inner temperature below 80°C until a residue volume of about 2600 1. About 3800 kg of a mixture, about 25/75 w/w acetic acid/toluene, which were sent to the incinerator, were distilled. The distillation residue crystallized at a temperature of about 40-50°C, then it was kept dissolved at the temperature of 50-60°C. In the meantime in a second reactor an ammoniacal solution was prepared by charging 656 kg of demineralized water and 1500 kg (1670 1) of an ammonia solution, about 28percent, were added thereto. By keeping the inner temperature at 10-25°C the distillation residue previously obtained and kept dissolved at 50-60°C (the addition was exothermic) was added. The pH was controlled which have to remain higher than a value of 8 during and at the end of the addition. The obtained biphasic solution was stirred for about 20 minutes at 20-30°C, then it was left to decant for one hour. The lower aqueous phase was separated, at room temperature, whereas the toluenic phase was sent to the incenerator. The aqueous phase was gradually vacuum-placed to remove possible toluene and ammonia traces. To the aqueous solution 3000 kg of demineralized water were added and the inner temperature was brought to 40-45°C. Then, by keeping the inner temperature at 40-45°C, about 1596 kg (1386 1) of hydrochloric acid in solution were added. It was left under stirring by still keeping the inner temperature of 40-45°C until obtaining pH 3.8-4. 2. At the end of the addition it was stirred for about 20 minutes and the pH was controlled again. By keeping the temperature at 40-45°C it was filtered and each filtration washed with four washings each one constituted by about 255 kg of demineralized water. About 2000 kg of wet product were obtained which was sent to the drying. The process yield was higher than 95percent. The titre of the reaction product evaluated by means of the HPLC method was greater than 99percent (total unknown impurities lower than 0.1percent). The resultant 1, 1-cyclohexanediacetic acid monoamide was transformed into gabapentin through known methods, for example, by the Hofmann rearrangement, the acidification, extraction, purification of an aqueous solution of gabapentin hydrochloride on a strong cationic ion exchange resin followed by recrystallization as described in the International patent application WO 02/34709 in the name of the same applicant
Example 1 Preparation of 1,1-Cyclohexanediacetic Acid Monoamide In 1.0 lit R B Flask charged water (135 ml), and ammonium chloride (161.6 g), under cooling. Aqueous sodium hydroxide solution (110 g in 200 ml water) was added drop wise under stirring maintaining temperature below 20° C. After complete addition the reaction mass was further maintained at 0-5° C. for 30 min. Charged 1,1-cyclohexane diacetic acid anhydride (100 gm) maintaining temperature below 5° C. Maintained the reaction mass for 2.0 hrs at about 0° C., then raised the temperature to 25-30° C. and maintained 2 hrs at room temperature. Adjusted pH of the solution to 2-3 with aqueous HCl. Cooled the reaction mass to 0° C., maintained for 1.0 hr, filtered the solid mass and washed with chilled water. Dried the wet cake to get 105 gm 1,1-Cyclohexanediacetic acid monoamide.
Example 3 Preparation of 1,1-Cyclohexanediacetic Acid Monoamide In 1.0 lit R B Flask charged 600 ml 12-14percent ammonia solution in isopropyl alcohol and cooled to 0° C. Slowly charged 1,1-cyclohexanediacetic acid anhydride (100 g) maintaining temperature below 5° C. Stirred 1.0 hr after complete addition and raised the temperature to room temperature. Then cooled to 15-20° C. and adjusted the pH to 2-3 with aq. HCl solution. The reaction mass was stirred further for about 15 hrs, Filtered and washed the solid with chilled water. Dried the wet cake to get 95 g 1,1-Cyclohexanediacetic acid monoamide. The filtrate was further concentrated to recover second crop 7 g.
Example 2 Preparation of 1,1-Cyclohexanediacetic Acid Monoamide In 1.0 lit R B Flask charged Toluene (500 ml) and 1,1-cyclohexanediacetic acid anhydride (100 gm). Heated the reaction mixture to 35-40° C. and charged slowly ammonium carbonate (47 g). Raised the temperature gradually to 70° C. and maintained for 6-8 hrs at ~70° C. Cooled the reaction mass to 0° C. and filtered the same. The solid obtained was taken in water and adjusted the pH to 2-3 with conc. HCl. The solution was cooled to 0° C. and maintained 2-3 hrs, filtered and washed with chilled water.
The 1,1-cyclohexanediacetic anhydride was added to 120 parts of benzene solvent, heated to 105 ° C, and the concentration of 20percent ammonia80 parts of water at 25 ° C ammoniation reaction 5h, cooling, separation of benzene solvent, add hydrochloric acid acidification to pH 4, heated to 55 ° C Stir1.5h, cooling, centrifugal filtration, the system 3,3-cyclopentane acid amide;

 

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