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

HRID 1618811Notes

Reaction equation

HRID 1618811 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16]Cl)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:18]=[N+:19]=[N-:20].[Na+]>CS(C)=O>[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:18]=[N+:19]=[N-:20])[CH2:10][CH2:9]1)([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 53412057tert-Butyl 4-(3-chloropropyl)piperazine-1-carboxylate

Product 1

HCID 86625340Tert-butyl 4-(3-azidopropyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

Tert-Butyl-4-(3-Chloropropyl)-1-piperazine carboxylate and sodium-azide were dissolved (suspended) in 8 ml DMSO dry and heated to 90° C. for 15 h. The reaction mixture was allowed to cool to room temperature and pored into 50 ml of water. The product was extracted with DCM and the combined organic phases dried over MgSO4. The product was purified by flash column chromatography (n-heptane/ethylacetate 1:1, RF=0.34). Yield: 3.5 g.

Workup

  1. customdry
  2. temperatureto cool to room temperature
  3. extractionThe product was extracted with DCM
  4. dry with materialthe combined organic phases dried over MgSO4
  5. customThe product was purified by flash column chromatography (n-heptane/ethylacetate 1:1, RF=0.34)

Sources & evidence

ORD record
ord-8b0799e26f6f48afbf58aa32af44d541
Source dataset
uspto-grants-2014_07
Patent number
US08771644B2

Reaction notes

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