Sodium Azide → 4-(Azidomethyl)-1-phenylpiperidin-2-one

HRID 341052Notes

Reaction equation

HRID 341052 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9](=[O:19])[CH2:8]1)(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+]>CS(C)=O.C(OCC)(=O)C>[N:20]([CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9](=[O:19])[CH2:8]1)=[N+:21]=[N-:22]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86668677(2-Oxo-1-phenylpiperidin-4-yl)methyl methanesulfonate

Product 1

HCID 866686784-(Azidomethyl)-1-phenylpiperidin-2-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2-oxo-1-phenylpiperidin-4yl)methyl methanesulfonate (0.37 g, 1.3 mmol) was dissolved in dimethylsulfoxide (6 mL), treated with sodium azide (0.18 g, 2.8 mmol, 2.1 equiv) and placed into a preheated oil bath at 60° C. for 18 hours. The mixture was cooled to ambient temperature, diluted with ethyl acetate (50 mL) and washed twice with water (50 mL) and brine (50 mL). The organic extract was dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Workup

  1. washwashed twice with water (50 mL) and brine (50 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4477f00a0cd14346968436b3e85e2df2
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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