1130-32-1

Basic information

• Product Name: 3,3-Pentamethylene glutarimide
• Synonyms: 3-AZASPIRO[4.5]DECAN-2-ONE;4,4-PENTAMETHYLENE-2-PYRROLIDINONE;3,3-Pentamethylene-2-Pyrrolidoinone;3,3-Pentamethylene-2-pyrrolidoinone(CAI) or 3-Azaspiro{5,5} undecane-2,4-dione;3,3-Pentamethylene;3,3-PENTAMETHYLENE GLUTARIMIDE(CAI);3-azaspiro(5,5)undecan-2,4-dione;beta,beta-pentamethylen-glutarsaeureimid
• CAS NO: 1130-32-1
• Molecular Formula: C₁₀H₁₅NO₂
• Molecular Weight: 181.23
• EINECS: 214-459-1
• Product Categories: INTERMEDIATESOFGABAPENTIN;(intermediate of gabapentin);Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1130-32-1.mol

Chemical Properties

• Melting Point: 84-89 °C(lit.)
• Boiling Point: 362.3 °C at 760 mmHg
• Flash Point: 161.2 °C
• Appearance: /Solid
• Density: 1.14 g/cm³
• Vapor Pressure: 1.96E-05mmHg at 25°C
• Refractive Index: 1.518
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 11.71±0.20(Predicted)
• CAS DataBase Reference: 3,3-Pentamethylene glutarimide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-Pentamethylene glutarimide(1130-32-1)
• EPA Substance Registry System: 3,3-Pentamethylene glutarimide(1130-32-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: CM0120000
• Hazardous Substances Data: 1130-32-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Gabapentin intermediate.

InChI:InChI=1/C10H15NO2/c12-8-6-10(7-9(13)11-8)4-2-1-3-5-10/h1-7H2,(H,11,12,13)

Upstream product

• 4355-11-7 1,1-cyclohexanediacetic acid 
• 77287-34-4 formamide 
• 1010-26-0 1,1-cyclohexanediacetic acid anhydride 
• 108-94-1 cyclohexanone 
• 372-09-8 cyanoacetic acid 
• 704-16-5 Cyanocarbamidomethylenecyclohexane 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 99189-60-3 [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid 
• 180-44-9 3-azaspiro[5.5]undecane 
• 60142-96-3 H-Gpn-OH 
• 1125-01-5 3-azaspiro[5.5]undecane hydrochloride 
• 64744-50-9 gabapentin-lactam 

Relevant articles and documents

Preparation method and application of 1-1 - cyclohexane - diacetic acid monoamide

The invention discloses a preparation method of 1-1 - cyclohexane - diacetic acid monoamide (CDMA), which comprises an amidation reaction of 1, 1 - cyclohexanedicarboxylic acid anhydride and 1 and 1 - cyclohexane - diacetic acid monoamide ammonium salt in a non-polar solvent of non-benzene to obtain 1, 1 - cyclohexane - diacetic acid monoamide (CDMA). Alternatively, in the non-polar solvent of non-benzene, 1, 1 - cyclohexanedicarboxylic anhydride is reacted with ammonia to heat reflux to give 3, 3 - cyclopentanediimides. 3,3 - Cycloglutarimide is obtained 1 by untying a base water, 1 - cyclohexane - diacetic acid monoamide (CDMA) wherein, with 1, 1 - cyclohexanedicarboxylic acid as a starting material, dehydration is carried out under acid catalysis to give 1, 1 - cyclohexanedicarboxylic acid anhydride.

Preparation method of gabapentin intermediate

The invention provides a preparation method of a gabapentin intermediate, and relates to the field of chemical organic synthesis. The preparation method comprises the following steps: taking cyanoacetic acid and cyclohexanone as raw materials, carrying out condensation, hydrolysis and decarboxylation reactions to obtain imide in an intermediate body, and further carrying out alkaline hydrolysis toobtain the intermediate cyclohexyl diacetate monoamide. The preparation method of the gabapentin intermediate provided by the invention has the advantages of readily available raw materials, mild reaction conditions, high safety factor, strong operability, simple process, easiness in industrialization, high product purity and stable quality.

AMIDOALKYLPIPERAZINYL DERIVATIVES FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISEASES

The invention relates to novel amidoalkylpiperazinyl derivatives of tricyclic heterocyclic systems of general formula (I), wherein Z represents -NH- and X represents -S-, or Z represents -S- and X represents >C=C1 represents H or -CH3, R6 and R7 both represent H, n is an integer from 0 to 4 inclusive, G represents a cyclic amide or imide moiety, and optical isomers, geometric isomers, and pharmaceutically acceptable salts thereof. The compounds may be useful for the treatment and/or prevention of the central nervous system disorders.

CRYSTALLINE FORMS OF GABAPENTIN AND PROCESS THEREOF

The present invention relates to crystalline forms of gabapentin and processes for preparing the same. The present invention particularly relates to crystalline forms of gabapentin form II and Form IIB. The invention also relates to gabapentin form IA and form IB. The gabapentin forms IA and IB are hydrated forma that contain about 20% of water by weight which corresponds to hemipentahydrate. The present invention also relates to the process for preparing these crystalline forms of gabapentin.

PROCESS FOR THE PREPARATION OF GABAPENTIN

The present invention relates to a process for the preparation of gabapentin and, more in particular, to a method of synthesis of 1,1-cyclohexane acetic acid monoamide, an intermediate used in the preparation of gabapentin, comprising the basic hydrolysis reaction of α,?-diaminocarbonyl-β,β-pentamethylene glutarimide.

PROCESS FOR PREPARING CYCLOHEXANEDIACETIC ACID MONOAMIDE

A new process is described for synthesising cyclohexanediacetic acid monoamide, a key compound in the synthesis of grabapentin precursors. The process of the invention is characterised by reacting cyclohexanone with cynoacetamide and immediately after, with a suitable malonic acid ester. A new intermediate (5-cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylic acid ester) is obtained which is convertible, under mild reaction conditions, into cyclohexanediacetic acid monoamide.

A PROCESS FOR SYNTHESIS OF 1-(AMINOMETHYL)CYCLOHEXANE ACETIC ACID HYDROCHLORIDE

A process for synthesis of 1-(aminomethyl)cyclohexane acetic acid hydrochloride (Gabapentin hydrochloride) comprising: a) Reaction of a mixture of acetic anhydride/ammonium acetate with 1,1-cyclohexane-diacetic acid to yield 3,3-pentamethylene glutarimide; b) Treatment of 3,3-pentamethylene glutarimide with sodium hydroxide in an aqueous solution up to dissolution, dripping the solution thus obtained into a to sodium hydroxide/sodium hypochlorite mixture, which is also aqueous, followed by acidification with hydrochloric acid to yield gabapentine hydrochloride.