29976-53-2

Basic information

• Product Name: N-Carbethoxy-4-piperidone
• Synonyms: 1-Ethoxycarbonyl-4-piperidone,99%;N-Ethoxycarbonyl-4-piperidone for synthesis;N-CARBETHOXY-4-PIPERIDONE;N-CARBOETHOXY-4-PIPERIDONE;N-ETHOXYCARBONYL-4-PIPERIDONE;AURORA KA-3057;ETHYL 4-PIPERIDONE-1-CARBOXYLATE;ETHYL 4-PIPERIDONE-N-CARBOXYLATE
• CAS NO: 29976-53-2
• Molecular Formula: C₈H₁₃NO₃
• Molecular Weight: 171.19
• EINECS: 249-984-5
• Product Categories: PHARMACEUTICAL INTERMEDIATES;Piperidines, Piperidones, Piperazines;Piperidine;(intermediate of loratadine);Boronic Acid;Heterocyclic Compounds;Heterocycles, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 29976-53-2.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 95-98 °C (1 mmHg)
• Flash Point: 190 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.135 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00574mmHg at 25°C
• Refractive Index: n20/D 1.475(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -1.59±0.20(Predicted)
• Water Solubility: slightly soluble
• BRN: 640967
• CAS DataBase Reference: N-Carbethoxy-4-piperidone(CAS DataBase Reference)
• NIST Chemistry Reference: N-Carbethoxy-4-piperidone(29976-53-2)
• EPA Substance Registry System: N-Carbethoxy-4-piperidone(29976-53-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/38-22-36/37/38-20/21/22
• Safety Statements: 23-24/25-37/39-26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 29976-53-2(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to pale yellow colored liquid

Uses

Different sources of media describe the Uses of 29976-53-2 differently. You can refer to the following data:
1. N-Carbethoxy-4-piperidone is used in the preparation of 3-hydrazinopyridazines as antihypertensive agents as well as γ-carboline derivatives as potential serotonergic agents. N-Carbethoxy-4-piperidone is also an Impurity of Loratadine (L469575).
2. N-Carbethoxy-4-piperidone (Loratadine EP Impurity H) is used in the preparation of 3-hydrazinopyridazines as antihypertensive agents as well as γ-carboline derivatives as potential serotonergic agents. N-Carbethoxy-4-piperidone is also an impurity of Loratadine (L469575).
3. Ethyl 4-oxo-1-piperidinecarboxylate (1-carbethoxy-4-piperidone) was used to prepare tertiary alcohols.

InChI:InChI=1/C8H13NO3/c1-2-12-8(11)9-5-3-7(10)4-6-9/h2-6H2,1H3

Upstream product

• 17759-76-1 ethyl 1-bromoformate 
• 41979-39-9 4-piperidone hydrochloride 
• 3518-88-5 3,3'-imino-di-propionic acid diethyl ester 
• 83783-66-8 Ethyl N-ethoxycarbonyl-3-(2-ethoxycarbonylethylamino)-propionate 
• 53601-94-8 4-oxo-piperidine-1,3-dicarboxylic acid diethyl ester 
• 79794-75-5 loratadine 
• 105-39-5 chloroacetic acid ethyl ester 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 541-41-3 chloroformic acid ethyl ester 
• 177-11-7 4,4-ethylenedioxy-piperidine 
• 51787-77-0 1,4-dioxa-8-aza-spiro[4.5]decane-8-carboxylic acid ethyl ester 
• 1445-73-4 1-Methyl-4-piperidone 

Downstream Products

• 100906-97-6 4-Benzoyloxy-4-isoquinolin-1-yl-piperidine-1-carboxylic acid ethyl ester 
• 37656-66-9 4-chloro-N-(1-ethoxycarbonyl-4-piperidinyl)aniline 
• 116512-92-6 N-(1-ethoxycarbonyl-4-piperidinyl)aniline 
• 16332-22-2 ethyl 4-hydroxy-4-phenylpiperidine-1-carboxylate 
• 102449-34-3 4-diphenylmethylene-1-piperidinecarboxylic acid ethyl ester 
• 121138-83-8 4-[(4-hydroxyphenyl)(N-ethyloxycarbonylpiperidin-4-ylidene)methyl]phenol 
• 96122-89-3 1-ethoxycarbonyl-4-(2-tolyl)piperidin-4-ol 
• 122858-43-9 ethyl 4-(4-bromo-2,5-difluorophenyl)-4-hydroxy-1-piperidinecarboxylate 
• 121138-84-9 4-[Bis-(4-acetoxy-phenyl)-methylene]-piperidine-1-carboxylic acid ethyl ester 
• 63277-57-6 ethyl 8-bromo-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate 
• 63277-54-3 ethyl 1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate 
• 61900-51-4 1-fluoro-2-phenylsulfanyl-benzene 
• 98796-27-1 1-(Ethoxycarbonyl)spiro(piperidine-4,6'-dibenz-1,4-oxathiepin) 
• 141376-39-8 4-Hydroxy-4-[3-(naphthalen-2-ylmethoxy)-phenyl]-piperidine-1-carboxylic acid ethyl ester 

Relevant articles and documents

Ecotoxic effects of loratadine and its metabolic and light-induced derivatives

Loratadine and desloratadine are second-generation antihistaminic drugs. Because of human administration, they are continuously released via excreta into wastewater treatment plants and occur in surface waters as residues and transformation products (TPs). Loratadine and desloratadine residues have been found at very low concentrations (ng/L) in the aquatic environment but their toxic effects are still not well known. Both drugs are light-sensitive even under environmentally simulated conditions and some of the photoproducts have been isolated and characterized. The aim of the present study was to investigate the acute and chronic ecotoxicity of loratadine, desloratadine and their light-induced transformation products in organisms of the aquatic trophic chain. Bioassays were performed in the alga Pseudokirchneriella subcapitata, the rotifer Brachionus calyciflorus and in two crustaceans, Thamnocephalus platyurus and Ceriodaphnia dubia. Loratadine exerted its acute and chronic toxicity especially on Ceriodaphnia dubia (LC50: 600 μg/L, EC50: 28.14 μg/L) while desloratadine showed similar acute toxicity among the organisms tested and it was the most chronically effective compound in Ceriodaphnia dubia and Pseudokirchneriella subcapitata. Generally, transformation products were less active in both acute and chronic assays.

Development of a Robust Process for the Preparation of High-Quality 4-Methylenepiperidine Hydrochloride

An efficient route for the preparation of 4-methylenepiperidine hydrochloride 1 was designed, and then a process feasible for large-scale production was developed with a total yield of 83.5% at a purity of 99.9%.

Penfluridol preparation method

The invention discloses a penfluridol preparation method. The penfluridol preparation method includes the following steps of 1), subjecting succinic anhydride and fluorobenzene to Friedel-Crafts reaction prior to acid decomposition, and collecting a compound from the formula 2) as is shown in the description; 2), putting the compound in a solvent to collect a compound in formula 3) as is shown in the description in a solvent reduced through a reducing agent; 3), putting the compound into the fluorobenzene to perform the Friedel-Crafts reaction to collect a compound in the formula 4) as is shown in the description; subjecting the compound and ethyl chloroformate to action to generate a compound in formula 5) as is shown in the description; 5), subjecting the compound and a compound shown in formula (XVII) to reaction prior to hydrolyzation to collect a compound in formula 6) as is shown in the description; 6), performing reduction with the reducing agent prior to hydrolyzing a reduction product and then collecting penfluridol (I). The penfluridol preparation method is high in yield, low in cost, moderate in reaction condition, short in circuit, proper for industrial production, low in three wastes, easy to treat and suitable for industrial production.