Methanesulfonyl chloride → 2-(N-methanesulfonyl-4-piperidinyloxy)-5-chloropyridine

HRID 2355146Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([S:25]([CH3:24])(=[O:27])=[O:26])[CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

Reactant 3

HCID 31297Methanesulfonyl chloride

HCID 81531Diisopropylethylamine

HCID 112643295-Chloro-2-(piperidin-4-yloxy)pyridine

Product 1

HCID 227197192-(N-methanesulfonyl-4-piperidinyloxy)-5-chloropyridineYield 74%

Procedure

5-Chloro-2-(piperidine-4-yloxy)-pyridine (2.13 g; 10 mmol) (preparation of this compound was made as described in WO 99-GB2801), diisopropylethylamine (2.20 ml; 12.5 mmol) and Methanesulfonyl chloride (1.56 ml; 10.1 mmol) gave 2.14 g (74%) of the title compound.

Sources & evidence

ORD record: ord-dd153951e50d4efdb4c98a4b65a6c759
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754750B2

Reaction notes

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