4-((Pyrrolidin-1-ylsulfonyl)methyl)aniline

Base Information

• Chemical Name: 4-((Pyrrolidin-1-ylsulfonyl)methyl)aniline
• CAS No.: 334981-10-1
• Molecular Formula: C11H16N2O2S
• Molecular Weight: 240.326
• Hs Code.: 2935009090
• UNII: 2EU666P9ND
• DSSTox Substance ID: DTXSID80458020
• Nikkaji Number: J1.455.241C
• Wikidata: Q72440716
• Mol file: 334981-10-1.mol

Synonyms:334981-10-1;4-((pyrrolidin-1-ylsulfonyl)methyl)aniline;4-(pyrrolidin-1-ylsulfonylmethyl)aniline;4-(Pyrrolidinosulfonylmethyl)benzeneamine;4-(PYRROLIDINE-1-SULFONYLMETHYL)ANILINE;1-((4-Aminobenzenemethane)sulfonyl)pyrrolidine;Pyrrolidine, 1-[[(4-aminophenyl)methyl]sulfonyl]-;1-[[(4-Aminophenyl)methyl]sulfonyl]-pyrrolidine;2EU666P9ND;4-[(1-Pyrrolidinylsulfonyl)methyl]benzenamine;4-[(1-pyrrolidinylsulfonyl)methyl]- Benzenamine;UNII-2EU666P9ND;4-((1-Pyrrolidinylsulfonyl)methyl)benzenamine;Benzenamine, 4-((1-pyrrolidinylsulfonyl)methyl)-;MFCD06795500;N-[(4-AMINOPHENYL)METHYL SULFONYL]PYRROLIDINE;4-(1-pyrrolidinylsulfonylmethyl)aniline;N-[(4-Aminophenyl)-methylsulfonyl]pyryolidine;4-[(1-pyrrolidinylsulfonyl)methyl]-Benzenamine;4-(Pyrrolidine-1-sulfonylmethyl)-phenylamine;N-[(4-Aminophenyl)methyl sulfonyl]pyryolidine;4-[(1-pyrrolidinylsulfonyl)methyl]phenylamine;1-[[(4-Aminophenyl)methyl]sulfonyl]pyrrolidine;SCHEMBL1425543;DTXSID80458020;VNSKHALYBQZMFW-UHFFFAOYSA-N;Pyrrolizino(4-aminobenzyl) sulfone;AMY13399;BCP10970;AKOS009159104;1-[(4-Aminobenzyl)sulfonyl]pyrrolidine;4-(pyrrolidine-1-sulfonylmethyl)-aniline;AC-25847;AS-15842;4-[(1-Pyrrolidinylsulfonyl)methyl]aniline;4-[(Pyrrolidine-1-sulfonyl)methyl]aniline;A5968;CS-0113418;FT-0648299;P2148;{4-[(pyrrolidin-1-ylsulfonyl)methyl]phenyl}amine;AR-011/42531548;4-(pyrrolidine-1-sulfonylmethyl)aniline, AldrichCPR;J-504080;Benzenamine, 4-[(1-pyrrolidinylsulfonyl)methyl]-;Pyrrolidine, 1-[[(4-aminophenyl)methyl]sulfonyl]- (9CI);4-(Pyrrolidin-1-ylsulfonylmethyl)aniline

Chemical Property of 4-((Pyrrolidin-1-ylsulfonyl)methyl)aniline

Chemical Property:

• Appearance/Colour: Pale yellow solid
• Vapor Pressure: 9.65E-08mmHg at 25°C
• Melting Point: 170-176 °C
• Refractive Index: 1.618
• Boiling Point: 434.2 °C at 760 mmHg
• PKA: 4.35±0.10(Predicted)
• Flash Point: 216.4 °C
• PSA: 71.78000
• Density: 1.31 g/cm³
• LogP: 2.79430
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 240.09324893
• Heavy Atom Count: 16
• Complexity: 309

Purity/Quality:

99% ^*data from raw suppliers

1-((4-Aminobenzenemethane)sulfonyl)pyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(C1)S(=O)(=O)CC2=CC=C(C=C2)N
• Uses: Intermediate in the preparation of Almotriptan.

Technology Process of 4-((Pyrrolidin-1-ylsulfonyl)methyl)aniline

There total 4 articles about 4-((Pyrrolidin-1-ylsulfonyl)methyl)aniline 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: 90.21%

1-(4-nitrophenylmethylsulfonyl)pyrrolidine (340041-91-0) → 4-((pyrrolidin-1-ylsulfonyl)methyl)aniline (334981-10-1)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; for 2h; under 3040.2 Torr; Reagent/catalyst; Solvent;

Reference yield:

(4-nitrophenyl)methanesulfonyl chloride (4025-75-6) → 4-((pyrrolidin-1-ylsulfonyl)methyl)aniline (334981-10-1)

Guidance literature:

Multi-step reaction with 2 steps

1: chloroform / 4 h / 20 °C

2: hydrogen / palladium 10% on activated carbon / methanol / 4 h

With hydrogen; palladium 10% on activated carbon; In methanol; chloroform;

Reference yield:

(4-nitrophenyl)-methanesulfonic acid (53992-33-9) → 4-((pyrrolidin-1-ylsulfonyl)methyl)aniline (334981-10-1)

Guidance literature:

Multi-step reaction with 3 steps

1: bis(trichloromethyl) carbonate; N,N-dimethyl-formamide / dichloromethane / 2 h / 60 °C

2: triethylamine / 1,2-dichloro-ethane / 2.52 h / 60 °C

3: 5%-palladium/activated carbon; hydrogen / ethanol / 2 h / 3040.2 Torr

With bis(trichloromethyl) carbonate; 5%-palladium/activated carbon; hydrogen; triethylamine; N,N-dimethyl-formamide; In ethanol; dichloromethane; 1,2-dichloro-ethane;

upstream raw materials:

1-(4-nitrophenylmethylsulfonyl)pyrrolidine

(4-nitrophenyl)methanesulfonyl chloride

(4-nitrophenyl)-methanesulfonic acid

Downstream raw materials:

almotriptan

3-methyl-1-(4-((pyrrolidin-1-ylsulfonyl)methyl)phenyl)-5-(thiophen-2-yl)-1H-pyrazole

C₂₁H₂₀F₃N₃O₂S

1-{[3-bromo-4-[N-(3-methoxycarbonyl-2-propenyl)trifluoroacetamido]phenyl]methylsulfonyl}pyrrolodine

Refernces

• 1、 -. "Preparation method of almotriptan key intermediate 1-(4-amino-phenylmethylsulfonyl)pyrrolidine". Paragraph 0042; 0047-0049; 0054-0056; 0061-0063; 0068-0070. . Retrieved 2018/09/12.
• 2、 -. "PREPARATION AND UTILITY OF SUBSTITUTED INDOLES". Page/Page column 39. . Retrieved 2008/06/13.