4-(3-Chloropyridin-2-yl)morpholine

Base Information

• Chemical Name: 4-(3-Chloropyridin-2-yl)morpholine
• CAS No.: 54231-36-6
• Molecular Formula: C9H11ClN2O
• Molecular Weight: 198.65
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID50384665
• Wikidata: Q72455556
• Mol file: 54231-36-6.mol

Synonyms:54231-36-6;4-(3-chloropyridin-2-yl)morpholine;3-Chloro-2-morpholinopyridine;3-CHLORO-2-(4-MORPHOLINO)PYRIDINE;4-(3-chloro-2-pyridinyl)morpholine;MFCD00498941;Maybridge2_000531;2-morpholino-3-chloropyridine;SCHEMBL164174;DTXSID50384665;HMS1304I03;STL284694;AKOS005203355;AM87050;AC-23672;SY014956;TS-02813;CS-0157015;N10070;J-513378

Chemical Property of 4-(3-Chloropyridin-2-yl)morpholine

Chemical Property:

• Boiling Point: 318.9±42.0 °C(Predicted)
• PKA: 3.29±0.10(Predicted)
• PSA: 25.36000
• Density: 1.257
• LogP: 1.63660
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 198.0559907
• Heavy Atom Count: 13
• Complexity: 162

Purity/Quality:

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

4-(3-Chloropyridin-2-yl)morpholine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCN1C2=C(C=CC=N2)Cl

Technology Process of 4-(3-Chloropyridin-2-yl)morpholine

There total 4 articles about 4-(3-Chloropyridin-2-yl)morpholine 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: 95.0%

4-(benzoyloxy)morpholine (5765-65-1) + (3-chloropyridin-2-yl)zinc pivalate → 4-(3-chloropyridin-2-yl)morpholine (54231-36-6)

Guidance literature:

With Li₂CoCl₄; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; at 25 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.201710931

Reference yield: 83.0%

morpholine (110-91-8,99108-56-2) + 2-bromo-3-chloropyridine (96424-68-9) → 4-(3-chloropyridin-2-yl)morpholine (54231-36-6)

Guidance literature:

With dichloro[4,5-bis(diphenylphosphino)-9,9’-dimethylxanthene]palladium(II); sodium t-butanolate; at 75 ℃; Inert atmosphere;

DOI:10.1002/chem.201902147

Reference yield:

2-iodo-3-pyridyl chloride (77332-89-9) → 4-(3-chloropyridin-2-yl)morpholine (54231-36-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,2,6,6-tetramethylpiperidinyl magnesium chloride-lithium chloride / tetrahydrofuran / 6 h / 0 °C / Schlenk technique; Inert atmosphere

1.2: 0.25 h / 0 - 25 °C / Schlenk technique; Inert atmosphere

2.1: N,N,N,N,-tetramethylethylenediamine; Li₂CoCl₄ / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere

With Li₂CoCl₄; N,N,N,N,-tetramethylethylenediamine; 2,2,6,6-tetramethylpiperidinyl magnesium chloride-lithium chloride; In tetrahydrofuran;

DOI:10.1002/anie.201710931

upstream raw materials:

morpholine

3-chloro-2-nitropyridine

4-(benzoyloxy)morpholine

2-iodo-3-pyridyl chloride

Refernces

• 1、 Chen, Yi-Hung,Gra?l, Simon,Knochel, Paul. "Cobalt-Catalyzed Electrophilic Amination of Aryl- and Heteroarylzinc Pivalates with N-Hydroxylamine Benzoates". supporting information. p. 1108 - 1111. Retrieved 2018/01/01.