Ammonium Chloride → tert-Butyl 3-azidopiperidine-1-carboxylate

HRID 1743006Notes

Reaction equation

HRID 1743006 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH:16](OS(C)(=O)=O)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>CN(C=O)C.O>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([N:1]=[N+:2]=[N-:3])[CH2:15]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 568122N-Boc-3-mesyloxypiperidine

Product 1

HCID 547722tert-Butyl 3-azidopiperidine-1-carboxylateYield 56.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

Sodium azide (6.96 g, 0.107 mol) and ammonium chloride (2.13 g, 0.0399 mol) were added to a solution of 1-(tert-butoxy carbonyl)3-[(methylsulphonyl)oxy]piperidine (10 g, 0.0358 mol) in DMF (75 ml) and water (12.5 ml). The mixture was heated overnight at 125° C. under stirring, cooled and diluted with water and extracted with chloroform. The organic layer was washed with water, dried over Na2SO4 and concentrated to give 4.6 g of thin reddish brown oil. 1H NMR (CDCl3) δ: 2.80-4.30 (m, 5H), 1.60-2.20 (m, 4H), 1.50 (s, 9H).

Workup

  1. temperaturecooled
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a7e833bf4c6b4922ae2e52e8ed4420da
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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