2-[Benzyl(methyl)amino]ethyl 3-oxobutanoate

Base Information

• Chemical Name: 2-[Benzyl(methyl)amino]ethyl 3-oxobutanoate
• CAS No.: 54527-65-0
• Molecular Formula: C14H19 N O3
• Molecular Weight: 249.31
• Hs Code.: 2922509090
• European Community (EC) Number: 259-197-9
• UNII: 64D7EYX3Z5
• DSSTox Substance ID: DTXSID20866428
• Nikkaji Number: J31.336J
• Mol file: 54527-65-0.mol

Synonyms:54527-65-0;2-[Benzyl(methyl)amino]ethyl 3-oxobutanoate;Butanoic acid, 3-oxo-, 2-[methyl(phenylmethyl)amino]ethyl ester;2-[Methyl(phenylmethyl)amino]ethyl 3-oxobutanoate;EINECS 259-197-9;2-(Benzylmethylamino)ethylacetoacetate;EC 259-197-9;64D7EYX3Z5;SCHEMBL3855356;DTXSID20866428;HPHPTGDPZSEYMB-UHFFFAOYSA-N;ACETOACETIC ACID N-BENZYL-N-METYL-2-AMINOETHYL ESTER;NS00009408;2-(N-benzyl-N-methylamino)ethyl acetoacetate;2-[Methyl(phenylmethyl)amino]ethyl 3-Oxo-butanoic Acid

Chemical Property of 2-[Benzyl(methyl)amino]ethyl 3-oxobutanoate

Chemical Property:

• Vapor Pressure: 4.74E-06mmHg at 25°C
• Boiling Point: 382.4°C at 760 mmHg
• PKA: 10.44±0.46(Predicted)
• Flash Point: 185.1°C
• PSA: 46.61000
• Density: 1.08g/cm³
• LogP: 1.64070
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 249.13649347
• Heavy Atom Count: 18
• Complexity: 272

Purity/Quality:

99.9% ^*data from raw suppliers

2-[Methyl(phenylmethyl)amino]ethyl3-Oxo-butanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC(=O)OCCN(C)CC1=CC=CC=C1
• Uses: Intermediate for the syntheses of different organic chemicals. Attributes Contact us for further information Contact 2-[Methyl(phenylmethyl)amino]ethyl 3-Oxo-butanoic Acid is used in the synthesis of Nicardipine O-Desmethyl-O-methyl(phenylmethyl)aminoethyl Ester Hydrochloride (N394510), which is a Nicardipine (N394500) impurity. Nicardipine is a dihydropyridine calcium channel blocker. Antianginal; Antihypertensive.

Technology Process of 2-[Benzyl(methyl)amino]ethyl 3-oxobutanoate

There total 4 articles about 2-[Benzyl(methyl)amino]ethyl 3-oxobutanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.6%

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) → acetoacetic acid [2-(N-methyl-N-benzylamino)-ethyl]-ester (54527-65-0)

Guidance literature:

With triethylamine; In chloroform; for 10h; Ambient temperature;

DOI:10.1248/cpb.43.797

Reference yield: 26.0%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + 2,2,6-trimethyl-4H-1,3-dioxin-4-one (5394-63-8) → acetoacetic acid [2-(N-methyl-N-benzylamino)-ethyl]-ester (54527-65-0)

Guidance literature:

With potassium acetate; at 130 ℃; for 0.333333h; Microwave irradiation;

DOI:10.1002/cmdc.201200417

Reference yield:

benzyl-methyl-amine (103-67-3) → acetoacetic acid [2-(N-methyl-N-benzylamino)-ethyl]-ester (54527-65-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / K₂CO₃ / dimethylformamide / 9 h / 60 °C

2: 63.6 percent / Et₃N / CHCl₃ / 10 h / Ambient temperature

With potassium carbonate; triethylamine; In chloroform; N,N-dimethyl-formamide;

DOI:10.1248/cpb.43.797

upstream raw materials:

4-methyleneoxetan-2-one

2-(N-benzyl-N-methyl)amino-1-ethanol

ethyl acetoacetate

benzyl-methyl-amine

Downstream raw materials:

1,4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 2-[methyl(phenylmethyl)amino]ethyl ester

2-(4-Methoxy-benzylsulfanyl)-6-methyl-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-pyrimidine-5-carboxylic acid 2-(benzyl-methyl-amino)-ethyl ester

2-(4-Methoxy-benzylsulfanyl)-4-methyl-6-(3-nitro-phenyl)-6H-pyrimidine-1,5-dicarboxylic acid 5-[2-(benzyl-methyl-amino)-ethyl] ester 1-ethyl ester

2-(4-Methoxy-benzylsulfanyl)-4-methyl-6-(2-trifluoromethyl-phenyl)-6H-pyrimidine-1,5-dicarboxylic acid 5-[2-(benzyl-methyl-amino)-ethyl] ester 1-ethyl ester

Refernces

• 1、 Hasegawa, Tadashi,Yasuda, Naoko,Yoshioka, Michikazu. "Photocyclization of 2-(dialkylamino)ethyl acetoacetates: Remote proton transfer and stern-volmer quenching kinetics in the system involving two reactive excited states". . p. 221 - 226. Retrieved 2007/10/03.
• 2、 Hernandez-Gallegos, Z.,Lehmann, P. A. F.,Hong, E.,Posadas, F.,Hernandez-Gallegos, E.. "Novel halogenated 1,4-dihydropyridines: synthesis, bioassay, microsomal oxidation and structure-activity relationships". . p. 355 - 364. Retrieved 2007/10/02.