4-Anilino-1-benzylpiperidine-4-carboxamide

Base Information

• Chemical Name: 4-Anilino-1-benzylpiperidine-4-carboxamide
• CAS No.: 1096-03-3
• Molecular Formula: C19H23 N3 O
• Molecular Weight: 309.411
• Hs Code.: 2933399090
• European Community (EC) Number: 214-141-2
• NSC Number: 73749
• UNII: YO1IP87NTP
• DSSTox Substance ID: DTXSID70148988
• Nikkaji Number: J217.211I
• Wikidata: Q83014653
• ChEMBL ID: CHEMBL387884
• Mol file: 1096-03-3.mol

Synonyms:1096-03-3;4-Anilino-1-benzylpiperidine-4-carboxamide;1-benzyl-4-(phenylamino)piperidine-4-carboxamide;4-(phenylamino)-1-benzyl-4-piperidinecarboxamide;YO1IP87NTP;4-anilino-1-benzyl-4-piperidinecarboxamide;EINECS 214-141-2;MFCD00474726;NSC-73749;NSC73749;UNII-YO1IP87NTP;ChemDiv3_014186;NCIOpen2_008848;Oprea1_701669;Oprea1_855958;MLS003960116;CHEMBL387884;QSPL 402;SCHEMBL2996293;DTXSID70148988;HMS1513E18;NSC 73749;STK504027;AKOS000265654;HS-0024;IDI1_029984;SMR001601276;SY084670;CS-0321355;FT-0673694;N-Benzyl-4-anilino-4-piperidine carboxamide;F11784;AE-641/03239053;SR-01000596968;J-002309;SR-01000596968-1;4-(Phenylamino)-1-(phenylmethyl)-4-piperidinecarboxamide;4-Piperidinecarboxamide, 4-(phenylamino)-1-(phenylmethyl)-;REMIFENTANIL HYDROCHLORIDE IMPURITY I [EP IMPURITY]

Chemical Property of 4-Anilino-1-benzylpiperidine-4-carboxamide

Chemical Property:

• Vapor Pressure: 4.95E-11mmHg at 25°C
• Melting Point: 186.8-188.2 °C
• Boiling Point: 522.9°Cat760mmHg
• PKA: 15.37±0.20(Predicted)
• Flash Point: 270.1°C
• PSA: 58.36000
• Density: 1.201g/cm³
• LogP: 3.32980
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 309.184112366
• Heavy Atom Count: 23
• Complexity: 378

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-(Phenylamino)-1-benzyl-4-piperidinecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCC1(C(=O)N)NC2=CC=CC=C2)CC3=CC=CC=C3
• Uses: 4-anilino-1-benzylpiperidine-4-carboxamide is used as modulators of muscarinic receptors for treatment of CNS disorders

Technology Process of 4-Anilino-1-benzylpiperidine-4-carboxamide

There total 10 articles about 4-Anilino-1-benzylpiperidine-4-carboxamide 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: 94.0%

1-benzyl-4-(phenylamino)piperidine-4-carbonitrile (968-86-5) → 1-benzyl-4-phenylaminopiperidine-4-carboxylic acid amide (1096-03-3)

Guidance literature:

With sulfuric acid; at 20 ℃; for 18h;

DOI:10.1021/acs.jmedchem.8b00278

Reference yield:

1-phenylmethyl-4-piperidone (3612-20-2) → 1-benzyl-4-phenylaminopiperidine-4-carboxylic acid amide (1096-03-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / aq. AcOH / 48 h / 20 °C

2: 77 percent / H₂SO₄ / 16 h / 20 °C

With sulfuric acid; acetic acid;

DOI:10.1021/jm0507274

Reference yield:

aniline (62-53-3) → 1-benzyl-4-phenylaminopiperidine-4-carboxylic acid amide (1096-03-3)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / isopropyl alcohol / 4 h / Cooling with ice; Reflux

2: sulfuric acid; trifluoroacetic acid / 16 h / 45 - 50 °C / Inert atmosphere

With sulfuric acid; acetic acid; trifluoroacetic acid; In isopropyl alcohol;

upstream raw materials:

1-benzyl-4-(phenylamino)piperidine-4-carbonitrile

1-phenylmethyl-4-piperidone

aniline

Downstream raw materials:

1-(phenylmethyl)-4,4-(2-phenyl-2,4-diaza-4-oxo-cyclopentane)piperidine

methyl 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate

1-benzyl-4-anilinoisonipecotic acid dihydrochloride

1-benzyl-4-[phenyl(propionyl)amino]piperidine-4-carboxylic acid

Refernces

• 1、 Taber, Douglass F.,Rahimizadeh, Mohammad. "Amide to Ester Conversion: A Practical Route to the Carfentanil Class of Analgetics". . p. 4037 - 4038. Retrieved 1992.
• 2、 Gong, Ping,Guo, Ming,Liu, Sicong,Miao, Xiuqi,Xing, Lingyun,Yin, Shiliang,Zhai, Xin,Zhang, Dajun,Zhang, Hong. "Design, synthesis and biological evaluation of 2-arylaminopyrimidine derivatives bearing 1,3,8-triazaspiro[4,5]decan-4-one or piperidine-3-carboxamide moiety as novel Type-I1/2 ALK inhibitors". . . Retrieved 2019/12/26.
• 3、 Morciano, Giampaolo,Preti, Delia,Pedriali, Gaia,Aquila, Giorgio,Missiroli, Sonia,Fantinati, Anna,Caroccia, Natascia,Pacifico, Salvatore,Bonora, Massimo,Talarico, Anna,Morganti, Claudia,Rizzo, Paola,Ferrari, Roberto,Wieckowski, Mariusz R.,Campo, Gianluca,Giorgi, Carlotta,Trapella, Claudio,Pinton, Paolo. "Discovery of Novel 1,3,8-Triazaspiro[4.5]decane Derivatives That Target the c Subunit of F1/FO-Adenosine Triphosphate (ATP) Synthase for the Treatment of Reperfusion Damage in Myocardial Infarction". supporting information. p. 7131 - 7143. Retrieved 2018/08/17.