Sodium Chloride → Tert-butyl 4-(3-azidopropyl)piperazine-1-carboxylate

HRID 1986161Notes

Reaction equation

HRID 1986161 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20]Br)[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].C(OCC)(=O)C.[Cl-].[Na+]>CN(C=O)C>[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][N:1]=[N+:2]=[N-:3])[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 15946517tert-Butyl 4-(3-bromopropyl)piperazine-1-carboxylate

Product 1

HCID 86625340Tert-butyl 4-(3-azidopropyl)piperazine-1-carboxylateYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (2.24 g, 34.2 mmol) is added to a stirred solution of 4-(3-bromo-propyl)-piperazine-1-carboxylic acid tert-butyl ester (4.80 g, 15.6 mmol) in anhydrous DMF (DMF) (40 mL). The resultant mixture is heated in an oil bath at 55° C. under nitrogen for 3 days. At ambient temperature, ethyl acetate (160 mL) and half-saturated aqueous sodium chloride (NaCl) (200 mL) are added to the mixture. The organic layer is separated, washed with half-saturated aqueous NaCl (200 mL), dried over magnesium sulfate, filtered, and concentrated to provide the title compound as a dark oil (3.88 g, 92% yield).

Workup

  1. customThe organic layer is separated
  2. washwashed with half-saturated aqueous NaCl (200 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3374e6becb9e449ba347afb23579679d
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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