76308-26-4

Basic information

• Product Name: Ethyl trans-2-(4-Aminocyclohexyl)acetate Hydrochloride
• Synonyms: Ethyl trans-2-(4-Aminocyclohexyl)acetate Hydrochloride;Cyclohexaneacetic acid, 4-aMino-,ethyl ester (hydrochloride)(1:1), trans-;Ethyl 2-(trans-4-aMinocyclohexyl)acetate hydrochloride;trans-4-Aminocyclohexaneacetic acid ethyl ester hydrochloride;trans-2-(4-Aminocyclohexyl)acetic acid ethyl ester hydrochloride;Ethyl 2-(trans-4-aminocyclohexyl);Ethyl trans-2-(4-aminocyclohexyl)acetate, HCl
• CAS NO: 76308-26-4
• Molecular Formula: C₁₀H₁₉NO₂*ClH
• Molecular Weight: 222
• Mol File: 76308-26-4.mol

Chemical Properties

• Melting Point: 177 °C
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Methanol (Slightly)
• CAS DataBase Reference: Ethyl trans-2-(4-Aminocyclohexyl)acetate Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl trans-2-(4-Aminocyclohexyl)acetate Hydrochloride(76308-26-4)
• EPA Substance Registry System: Ethyl trans-2-(4-Aminocyclohexyl)acetate Hydrochloride(76308-26-4)

Safety Data

• Hazardous Substances Data: 76308-26-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Ethyl trans-2-(4-Aminocyclohexyl)acetate Hydrochloride is used as an organic synthesis intermediate for the preparation of various complex organic molecules. Its unique structure allows for the formation of new chemical bonds and the synthesis of a wide range of compounds, making it a valuable component in the development of novel organic materials.
Used in Pharmaceutical Industry:
Ethyl trans-2-(4-Aminocyclohexyl)acetate Hydrochloride is used as a pharmaceutical intermediate, playing a crucial role in the synthesis of various pharmaceutical compounds. Its presence in the molecular structure of target drugs can contribute to their therapeutic properties, such as enhancing their efficacy, bioavailability, or stability.
Used in Laboratory Research and Development:
Ethyl trans-2-(4-Aminocyclohexyl)acetate Hydrochloride is utilized in laboratory research and development processes to explore its potential applications and to study its chemical properties. Researchers use this compound to investigate new reaction pathways, develop innovative synthetic methods, and understand its reactivity with other molecules.
Used in Chemical Production Processes:
Ethyl trans-2-(4-Aminocyclohexyl)acetate Hydrochloride is employed in chemical production processes to manufacture a variety of chemical products. Its versatility as an intermediate allows for the efficient synthesis of target compounds on a larger scale, contributing to the advancement of the chemical industry.

Synthesis

Preparation of trans 4-amino-cyclohexyl-acetic acid ethyl ester HClA 2500 1 enamelled autoclave is charged with 1000 kg of deionizated water and 210 kg (1.16 kM) of 4-nitrophenyl-acetic acid at room temperature under nitrogen atmosphere. After inertisation by nitrogen to the mixture obtained a suspension of 21 kg of 10% Pd/C in 20 kg of deionized water is added and the catalyst measuring gauge is rinsed by additional 20 kg of deionizated water. After rinsing the reaction vessel by hydrogen gas the hydrogenation is carried out at a temperature between 44-46°C and under up to 0,6 bar overpressure until the hydrogen uptake is slowed. After reducing the nitro group the temperature is brought to 55- 58°C and the hydrogenation continued maintaining hydrogen pressure on max. 4.0 bar overpressures. After completion of the hydrogen uptake, the mixture is cooled to a temperature between 25-30°C, purged with nitrogen and the catalyst is filtered on a Spakler filter under pressurized nitrogen. The reaction vessel, the filter and the lines are washed additional 200 g of deionized water. The filtrates are combined and in a 2500 1 enamelled doubler 1200 kg of distillate is distilled at up to 80°C inner temperature in vacuum. The residue obtained is cooled to a temperature below 30°C and 430 kg of ethyl alcohol is added, then 500 1 of distillate is collected at up to 80°C under vacuum. After completion of the distillation the mixture is cooled to a temperature between 25-30°C, (water content is max. 10 w%, in terms of absolute value is about 32 kg), and 550 kg of ethyl alcohol, then 170 kg of 30% hydrochloric ethyl alcohol are added and the reaction mixture is heated to reflux for approx. 2 hours. When the esterification is complete 800 1 of solvent is distilled off at up to 80°C, under vacuum. Additional 800 1 of ethyl alcohol is added and further 750-800 1 of solvent is distilled off at up to 80°C, under vacuum. To the residue obtained 700 kg of acetonitrile is added and 140 1 of distillate is collected at up to 80°C under vacuum. The vacuum is stopped by introducing nitrogen and the solution is cooled to a temperature between 0-(-)5°C. The crystals obtained is centrifuged, washed with 100 kg of acetonitrile in two portions during which the temperature is kept at 0-(-)5°C. The solid obtained is dried to a constant weight at up to 6O0C. In this manner 90 kg of title product is obtained. Yield: 40 %. Melting point: 173-1760C.

InChI:InChI=1/C10H19NO2.ClH/c1-2-13-10(12)7-8-3-5-9(11)6-4-8;/h8-9H,2-7,11H2,1H3;1H/t8-,9-;

Upstream product

• 64-17-5 ethanol 
• 104-03-0 4-nitrobenzeneacetic acid 
• 1197-54-2 trans-(4-amino-cyclohexyl)-acetic acid 
• 5445-26-1 ETHYL 4-NITROPHENYLACETATE 
• 76325-96-7 trans-4-aminocyclohexylacetic acid hydrochloride 

Downstream Products

• 76308-31-1 N-phthalyl-trans-4-aminocyclohexylacetic acid ethyl ester 
• 189153-07-9 [4-(Pyrimidin-2-ylamino)-cyclohexyl]-acetic acid ethyl ester 
• 189153-09-1 [4-(2-Bromo-ethyl)-cyclohexyl]-pyrimidin-2-yl-amine 
• 189153-08-0 2-[4-(Pyrimidin-2-ylamino)-cyclohexyl]-ethanol 
• 946598-99-8 trans-ethyl 2-(4-acetamidocyclohexyl)acetate 
• 1221227-58-2 (trans-4-{2-cyclohexyl-2-[5-fluoro-2-((R)-methoxy-phenyl-methyl)-benzoimidazol-1-yl]-acetylamino}-cyclohexyl)-acetic acid ethyl ester 
• 1607590-79-3 ethyl {trans-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}acetate 
• 1613269-84-3 ethyl 2-(trans-4-((2-((tert-butoxycarbonyl)amino)ethyl)amino)cyclohexyl)acetate 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF TRANS 4-AMINO-CYCLOHEXYL ACETIC ACID ETHYL ESTER HCL

The invention relates to a process for the preparation of trans 4-amino-cyclohexil ethyl acetate HCl wherein d) hydrogenating 4-nitrophenyl acetic acid in a protic solvent at a temperature between 40-500C in the presence of Pd/C under 0.1-0.6 bar overpres

BENZOYL-PIPERIDINE DERIVATIVES AS DUAL MODULATORS OF THE 5-HT2A AND D3 RECEPTORS

The present invention relates to compounds of formula (I) wherein R1 and A are as defined in the specification as dual modulators of the serotonin 5-HT2a and dopamine D3 receptors, their manufacture, pharmaceutical compositions containing them and their use as medicaments. Compounds of general formula (I) have high affinity for the dopamine D3 and serotonin (5-Hydroxytryptamine; 5-HT) 5-HT2A receptors and are effective in the treatment of psychotic disorders, as well as other diseases such as depression and anxiety, drug dependence, dementias and memory impairment.

Aminopyrimidines with high affinity for both serotonin and dopamine receptors

A series of {4-[2-(4-arylpiperazin-1-yl)alkyl]cyclohexyl}pyrimidin-2- ylamines was prepared and found to have receptor binding affinity for D2 and D3 dopamine (DA) receptors and serotonin 5-HT1A receptors. The structural contributions to D2/D3 and 5-HT1A