Sodium Azide → 2-[4-(2-Azidoethyl)-1-piperidinyl]-6-chloroquinoline

HRID 1019692Notes

Reaction equation

HRID 1019692 reaction equation
CS(O[CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:24])[CH:20]=3)[N:15]=2)[CH2:10][CH2:9]1)(=O)=O.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C)C=O>[N:25]([CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:24])[CH:20]=3)[N:15]=2)[CH2:10][CH2:9]1)=[N+:26]=[N-:27]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 21096927HCID 21096927, compound

Product 1

HCID 866613392-[4-(2-Azidoethyl)-1-piperidinyl]-6-chloroquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5 g (13.55 mmol) of 2-[1-(6-chloroquinolin-2-yl)piperidin-4-yl]ethyl methanesulfonate, prepared in step 6.1., and 1.76 g (27.11 mmol) of sodium azide in 30 mL of N,N-dimethylformamide is refluxed for 4 hours, under an inert atmosphere.

Sources & evidence

ORD record
ord-0758aecb2e2c428ea618d0ce6aa09077
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

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