Sodium Azide → Ethyl 4-(4-azidopiperidin-1-yl)benzoate

HRID 591606Notes

Reaction equation

HRID 591606 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(=O)=O.[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C=O)C.[Cl-].[Na+].O>[N:23]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[N+:24]=[N-:25]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86662015HCID 86662015, compound

Product 1

HCID 86662016Ethyl 4-(4-azidopiperidin-1-yl)benzoateYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 4-(4-(methylsulfonyloxy)piperidin-1-yl)benzoate (10.5 g, 32.1 mmol) in DMF (50 mL) was added sodium azide (4.17 g, 64.2 mmol). The mixture was heated at 80° C. for 5 hours, cooled to room temperature, diluted with brine (300 mL), and extracted with ethyl acetate (400 mL). The organic phase was washed with brine (2×300 mL), dried over anhydrous MgSO4, filtered, and concentrated, to afford ethyl 4-(4-azidopiperidin-1-yl)benzoate as a yellow solid (7.62 g, 87%).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (400 mL)
  3. washThe organic phase was washed with brine (2×300 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-812e8beb9d2a47bfa20ec2b47e93414f
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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