Water → tert-Butyl 4-(3-chloropropyl)piperazine-1-carboxylate

HRID 1618810Notes

Reaction equation

HRID 1618810 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:15][CH2:16][CH2:17][Cl:18].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH2:17][Cl:18])[CH2:10][CH2:9]1)([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4.94 g tert-Butyl-1-piperazine-carboxylate and 12.66 g 1-Bromo-3-chloropropane in 15 ml DMF (dry) was added 4.08 g K2CO3 and the reaction heated to 50° C. for one minute and stirred at room temperature for additional 3 h. The reaction mixture is pored into 200 ml of water and extracted with DCM. The combined organic phases were washed with water and dried over MgSO4 and evaporated in vacuo. The product was purified by flash column chromatography (n-heptane/ethylacetate 1:1, RF=0.3) Yield 3.9 g.

Workup

  1. extractionextracted with DCM
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe product was purified by flash column chromatography (n-heptane/ethylacetate 1:1, RF=0.3) Yield 3.9 g

Sources & evidence

ORD record
ord-49e44022ee1a44cb8badb5318fca757a
Source dataset
uspto-grants-2014_07
Patent number
US08771644B2

Reaction notes

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