775-16-6

Basic information

• Product Name: 1-Benzyl-3-pyrrolidinone
• Synonyms: 1-BENZYL-3-PYRROLIDINONE;1-BENZYL-3-PYRROLIDONE;1-BENZYLPYRROLIDIN-3-ONE;1-(PHENYLMETHYL)-3-PYRROLIDINONE;N-BENZYL-3-PYRROLIDONE;N-BeNzyl-3-pyrrolidiNoNe;5 N-Benzyl-3-Pyrrolidone;1-BENZLY-3-PYRROLIDONE
• CAS NO: 775-16-6
• Molecular Formula: C₁₁H₁₃NO
• Molecular Weight: 175.23
• EINECS: 212-274-0
• Product Categories: Amines and Anilines;Carbonyl Compounds;Pyrrole&Pyrrolidine&Pyrroline;Building Blocks;Heterocyclic Building Blocks;Pyrrolidines;Pharmaceutical Intermediates;Building Blocks;C11 to C12;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 775-16-6.mol

Chemical Properties

• Boiling Point: 77 °C0.01 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to off-white/Crystalline Powder, Crystals or Chunks
• Density: 1.091 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.38E-05mmHg at 25°C
• Refractive Index: n20/D 1.539(lit.)
• Storage Temp.: 2-8°C
• PKA: 5.56±0.20(Predicted)
• BRN: 1526217
• CAS DataBase Reference: 1-Benzyl-3-pyrrolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyl-3-pyrrolidinone(775-16-6)
• EPA Substance Registry System: 1-Benzyl-3-pyrrolidinone(775-16-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-24/25-36
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 775-16-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Benzyl-3-pyrrolidinone is used as a starting reagent for the synthesis of chiral, alkenyl sulfoximines, which are key intermediates in the production of highly functionalized diazabicycles. These diazabicycles have potential applications in the development of novel pharmaceuticals and therapeutic agents.
Used in Chemical Synthesis:
1-Benzyl-3-pyrrolidinone is used as a substrate in the synthesis of vinyl triflate, a valuable intermediate in organic chemistry. 1-Benzyl-3-pyrrolidinone can be further transformed into a wide range of chemical products, demonstrating the versatility of 1-Benzyl-3-pyrrolidinone in various chemical reactions and applications.

InChI:InChI=1/C11H13NO/c13-11-6-7-12(9-11)8-10-4-2-1-3-5-10/h1-5H,6-9H2/p+1

Upstream product

• 96-42-4 pyrrolidin-3-one 
• 100-51-6 benzyl alcohol 
• 101385-90-4 (R)-N-benzyl-3-hydroxypyrrolidine 
• 100-46-9 benzylamine 
• 775-15-5 1-benzyl-3-pyrrolidinol 
• 155622-69-8 bromomethyl vinyl ketone 
• 107771-02-8 3-benzylamino-N,N-diethyl-propionamide 
• 86269-11-6 (Tributylstannyl)methyl methanesulfonate 

Downstream Products

• 96567-93-0 1-benzyl-3-methylpyrrolidin-3-ol 
• 562824-93-5 N-(1-benzyl-pyrrolidin-3-ylidene)-N'-(2-nitro-phenyl)-hydrazine 
• 145090-28-4 3-Amino-1-benzyl-pyrrolidine-3-carbonitrile 
• 209902-32-9 4-[N-(1-benzyl-pyrrolidin-3-yl)-amino]-N,N-diethyl benzamide 
• 1092573-59-5 1-benzyl-3-(3,5-difluorophenyl)-3-hydroxypyrrolidine 
• 863561-74-4 C₃₈H₄₈N₄OS 
• 1107638-84-5 C₂₂H₃₅N₃ 
• 1018442-96-0 1-Benzyl-3-isopropylpyrrolidin-3-ol 
• 79227-66-0 1-benzyl-3-[(o-fluorophenyl)-(1-pyrryl)methyl]-3-pyrrolidinol 
• 95274-12-7 N-Benzyl-3-(carbomethoxymethyl)pyrrolidine 
• 1292303-81-1 tert-butyl 2-(1-benzylpyrrolidin-3-yl)hydrazinecarboxylate 
• 868609-25-0 1-(1-benzyl-pyrrolidin-3-yl)-4-methyl-piperidine 
• 101385-93-7 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 97266-84-7 5-benzyl-1-oxa-5-azaspiro[2.4]heptane 

Relevant articles and documents

Synthesis method of 3-aminopyrrolidine dihydrochloride

The invention discloses a synthetic method of 3-aminopyrrolidine dihydrochloride. The synthetic method comprises the following steps: preparing benzyl-(3-ethoxy-3-alkenyl)-(1-vinyl ethoxy methyl) amine liquid; preparation of a 1-benzyl-3-pyrrolidone solution; preparation of a 1-benzyl-3-aminopyrrolidine solution; preparing a 1-benzyl-3-aminopyrrolidine salt; preparing a 3-aminopyrrolidine solution; the yield and purity of the 3-aminopyrrolidine dihydrochloride are improved by controlling the activity of the reaction main materials of each part in a segmented manner and carrying out a directional hydrogenation manner.

Scalable preparation of stable and reusable silica supported palladium nanoparticles as catalysts for N-alkylation of amines with alcohols

The development of nanoparticles-based heterogeneous catalysts continues to be of scientific and industrial interest for the advancement of sustainable chemical processes. Notably, up-scaling the production of catalysts to sustain unique structural features, activities and selectivities is highly important and remains challenging. Herein, we report the expedient synthesis of Pd-nanoparticles as amination catalysts by the reduction of simple palladium salt on commercial silica using molecular hydrogen. The resulting Pd-nanoparticles constitute stable and reusable catalysts for the synthesis of various N-alkyl amines using borrowing hydrogen technology without the use of any base or additive. By applying this Pd-based catalyst, functionalized and structurally diverse N-alkylated amines as well as some selected drug molecules were synthesized in good to excellent yields. Practical and synthetic utility of this Pd-based amination protocol has been demonstrated by upscaling catalyst preparation and amination reactions to several grams-scales as well as recycling of catalyst. Noteworthy, this Pd-catalyst preparation has been up-scaled to kilogram scale and catalysts prepared in both small (1 g) and large-scale (kg) exhibited similar structural features and activity.

Chemoselective Continuous Ru-Catalyzed Hydrogen-Transfer Oppenauer-Type Oxidation of Secondary Alcohols

A continuous flow method for the selective oxidation of secondary alcohols is reported. The method is based on an Oppenauer-type ruthenium-catalyzed hydrogen-transfer process that uses acetone as both solvent and oxidant. The process utilizes a low loading (1 mol%) of the commercially available ruthenium catalyst [Ru(p-cymene)Cl2]2 and triethylamine as a base and can be successfully applied to a range of different substrates, with a good level of functional group tolerance.

Preparation method of 5-benzyl-5-N spiro[2. 4]heptane-1-carboxylic acid

The invention discloses a preparation method of 5-benzyl-5-N spiro[2. 4]heptane-1-carboxylic acid. The preparation method comprises that through a series of Swern oxidation reaction, Wittig reaction, sulfur ylide reaction and hydrolysis reaction, 5-benzyl-5-N spiro[2. 4]heptane-1-carboxylic acid is prepared from 1-benzyl-3-hydroxypyrrolidine. The preparation method utilizes a reaction of the double bond and the sulfur ylide to produce the ternary ring, utilizes cheap and easily available raw materials, has mild conditions, utilizes a simple operation way and greatly improves the possibility of industrialization.

Identification of a novel class of succinyl-nitrile-based Cathepsin S inhibitors

The synthesis and in vitro activities of a series of succinyl-nitrile-based inhibitors of Cathepsin S are described. Several members of this class show nanomolar inhibition of the target enzyme as well as cellular potency. The inhibitors displaying the greatest potency contain N-alkyl substituted piperidine and pyrrolidine rings spiro-fused to the α-carbon of the P1 residue.

Heterocyclization of oximes of 3,5-dimethyl(1,3,5-trimethyl)-2,6- diphenylpiperid-4-ones and N-benzylpyrrolid-3-ones with acetylene in a superbasic medium

It has been established that on heterocyclization of 3,5-dimethyl-2,6- diphenylpiperid-4-one oxime with acetylene in a superbasic medium migration of the 3a-CH3 group to the anionic nitrogen atom occurs, leading to the formation of 5,7-dimethyl-4,6-diphenyl-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridine. The formation of the N-anion causes aromatization of the tetrahydropyridine ring. Tetrahydropyrrolo-[1,2-c]pyrimidines are formed in the Trofimov reaction as a result of decomposition of the intermediate 3H-pyrrole in a retro-Mannich reaction.

Investigation of 1-bromo-3-buten-2-one as building block in organic synthesis

1-Bromo-3-buten-2-one is investigated as a building block for organic synthesis. Reduction to the corresponding alcohol works best with lithium aluminium hydride, reaction with primary amines gives 5-membered-aza-heterocycles in moderate yields and reaction with activated methylene compounds to form 5-membered-carbocycles gave unsatisfactory yields when a one-pot-procedure was used. The first step of a stepwise protocol, a Michael addition, is discussed.

Synthesis of pyrrolidines by anionic cyclization onto allylic ethers, alkynes and carboxylic groups

α-Amino-methylstannanes with pendent allylic ether, alkyne or carboxylic groups, can be converted, on treatment with butyllithium, to 3-vinyl-, 3-methylene- or 3-keto-pyrrolidines by anionic cyclization.

6,7-dihydropyrrol[3,4-c]pyrido[2,3-d]pyrimidine derivatives

The present invention concerns compounds of the formula: STR1 wherein R is a lower alkyl group, an aryl group or an alkylaryl group and X and Y are the same or different, and each is OH, NH2, or SH. The aryl group or the aryl moiety of the alkylaryl group may be unsubstituted, monosubstituted, disubstituted or trisubstituted. If substituted, each substituent may independently be an alkyl group, an alkyloxy group or a halogen. The present invention also provides methods for synthesizing the compounds described above.