Methyl 2-(pyrrolidin-1-ylmethyl)isonicotinate

Base Information

• Chemical Name: Methyl 2-(pyrrolidin-1-ylmethyl)isonicotinate
• CAS No.: 125104-37-2
• Molecular Formula: C12H16N2O2
• Molecular Weight: 220.26800
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID101212900
• Mol file: 125104-37-2.mol

Synonyms:Methyl 2-(pyrrolidin-1-ylmethyl)isonicotinate;125104-37-2;Methyl 2-(1-pyrrolidinylmethyl)-4-pyridinecarboxylate;METHYL 2-(PYRROLIDIN-1-YLMETHYL)PYRIDINE-4-CARBOXYLATE;SCHEMBL9736097;OAIQKJZUUQREHD-UHFFFAOYSA-N;DTXSID101212900;Methyl2-(pyrrolidin-1-ylmethyl)isonicotinate

Chemical Property of Methyl 2-(pyrrolidin-1-ylmethyl)isonicotinate

Chemical Property:

• Boiling Point: 317.3±32.0 °C(Predicted)
• PKA: 8.53±0.20(Predicted)
• PSA: 42.43000
• Density: 1.164±0.06 g/cm3(Predicted)
• LogP: 1.40190
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 220.121177757
• Heavy Atom Count: 16
• Complexity: 239

Purity/Quality:

97%+ ^*data from raw suppliers

Methyl2-(pyrrolidin-1-ylmethyl)isonicotinate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=NC=C1)CN2CCCC2

Technology Process of Methyl 2-(pyrrolidin-1-ylmethyl)isonicotinate

There total 3 articles about Methyl 2-(pyrrolidin-1-ylmethyl)isonicotinate 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: 64.0%

pyrrolidine (123-75-1) + methyl 2-(chloromethyl)-4-pyridinecarboxylate hydrochloride (125398-17-6) → methyl 2-(1-pyrrolidinylmethyl)-4-pyridinecarboxylate (125104-37-2)

Guidance literature:

With triethylamine; In dichloromethane; 1.) -60 deg C, 1 h, 2.) RT, 72 h;

DOI:10.1021/jm00081a009

Reference yield:

methyl 2-(hydroxymethyl)pyridine-4-carboxylate (58481-17-7) → methyl 2-(1-pyrrolidinylmethyl)-4-pyridinecarboxylate (125104-37-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / etheral HCl, SOCl₂ / 4 h / 0 - 20 °C

2: 64 percent / Et₃N / CH₂Cl₂ / 1.) -60 deg C, 1 h, 2.) RT, 72 h

With hydrogenchloride; thionyl chloride; triethylamine; In dichloromethane;

DOI:10.1021/jm00081a009

Reference yield:

→ methyl 2-(1-pyrrolidinylmethyl)-4-pyridinecarboxylate (125104-37-2)

Guidance literature:

upstream raw materials:

pyrrolidine

methyl 2-(chloromethyl)-4-pyridinecarboxylate hydrochloride

methyl 2-(hydroxymethyl)pyridine-4-carboxylate

Downstream raw materials:

cis-methyl 1-<(3,4-dichlorophenyl)acetyl>-2-(1-pyrrolidinylmethyl)-4-piperidinecarboxylate

7-<(3,4-dichlorophenyl)acetyl>-8-(1-pyrrolidinylmethyl)-7-aza-1,4-dioxaspiro<4.5>decane

1-<(3,4-dichlorophenyl)acetyl>-6-(1-pyrrolidinylmethyl)-3-piperidinone

cis-methyl 1-<(3,4-dichlorophenyl)acetyl>-2-(1-pyrrolidinylmethyl)-4-piperidinecarboxamide

Refernces

• 1、 -. "SPIROPIPERIDINE DERIVATIVES". . . Retrieved 2008/06/13.