Ammonium Chloride → Tert-butyl 4-(2H-tetrazol-5-YL)piperidine-1-carboxylate

HRID 278235

Reaction equation

HRID 278235 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[N:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:16]=[N+:17]=[N-:18].[Na+].[Cl-].[NH4+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:18][N:17]=[N:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylate

Product 1

HCID 18187701Tert-butyl 4-(2H-tetrazol-5-YL)piperidine-1-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.10 g (10.0 mmol) of 1-(t-butoxycarbonyl)-4-cyanopiperidine (from Step A), 1.95 g (30.0 mmol) of sodium azide and 1.60 g (30.0 mmol) of ammonium chloride in 20 mL of DMF was stirred at 100° C. for 20 h. The mixture was cooled and partitioned between 200 mL of methylene chloride and 200 mL of 1.0 N HCl and the layers were separated. The organic layer was washed with 200 mL of water, dried over magnesium sulfate and concentrated. Flash chromatography on 50 g of silica gel using 4:1 v/v methylene chloride/ethyl acetate+1% acetic acid, then 2:1 v/v methylene chloride/ethyl acetate+1% acetic acid as the eluent afforded 1.51 g (60%) of the title compound:

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between 200 mL of methylene chloride and 200 mL of 1.0 N HCl
  3. customthe layers were separated
  4. washThe organic layer was washed with 200 mL of water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-204f252feebe4f45bd2e18f59a724327
Source dataset
uspto-grants-2002_03
Patent number
US06358979B1

Linked notes

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