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Sodium Azide → tert-Butyl 4-(azidomethyl)piperidine-1-carboxylate

HRID 1506929
Notes
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Reaction equation

HRID 1506929 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O>[N:20]([CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)=[N+:21]=[N-:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

Product 1

HCID 23282921tert-Butyl 4-(azidomethyl)piperidine-1-carboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Tertiary butyl 4-((methylsulfonyloxy)methyl)piperidine-1-carboxylate (48 g, 163.6 mmol) was dissolved in dimethylformamide (500 mL) and sodium azide (19.15 g, 295 mmol) was added thereto, followed by stirring at 120° C. for 6 hours. After the reaction was completed, the reactants were cooled to room temperature, extracted with ethyl acetate and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford the title compound (35 g, 89%).

Workup

  1. temperaturethe reactants were cooled to room temperature
  2. extractionextracted with ethyl acetate and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6eea9a64e8294f808e8bc6c0d380c7c5
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09221790B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes