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

HRID 1593007Notes

Reaction equation

HRID 1593007 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].[N-:16]=[N+:17]=[N-:18].[Na+].[Cl-].[NH4+]>CN(C)C=O>[N:2]1[NH:16][N:17]=[N:18][C:1]=1[CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1

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 51.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl 4-cyanopiperidine-1-carboxylate (2.1 g), sodium azide (1.95 g) and ammonium chloride (1.6 g) in dimethylformamide was heated to 100° C. for 18 hours. The mixture was cooled and partitioned between 1N HCl and dichloromethane. The organic layer was washed with water, dried (MgSO4) and evaporated to give a gum which was purified by column chromatography eluting with MeOH/dichloromethane (1:99) to give tert-butyl 4-(2H-tetrazol-5-yl)piperidine-1-carboxylate (1.31 g); NMR (CDCl3): 1.5 (s, 9H), 1.9 (m, 2H), 2.15 (m, 2H), 3.0 (m, 2H), 3.3 (m, 1H), 4.2 (m, 2H).

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between 1N HCl and dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a gum which
  7. customwas purified by column chromatography
  8. washeluting with MeOH/dichloromethane (1:99)

Sources & evidence

ORD record
ord-36d5a8b56b9c4d7fb14b07938f106c3e
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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