1-Bromo-3-chloropropane → Ethyl 4-(3-chloropropyl)piperazine-1-carboxylate

HRID 272832Notes

Reaction equation

HRID 272832 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH2:20][CH2:21][Cl:22]>CN(C=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([CH2:19][CH2:20][CH2:21][Cl:22])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 11430Potassium Carbonate

Product 1

HCID 410641Ethyl 4-(3-chloropropyl)piperazine-1-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Piperazine-1-carboxylic acid ethyl ester (3.0 g, 18.9 mmol), K2CO3 (2.8 g, 1.1 eq.), DMF (30 ml, 10 vol) and 1-bromo-3-chloropropane (1.8 ml, 18.9 mmol, 1 eq.) were reacted together at room temperature overnight. The reaction was quenched with water (100 ml) and extracted with DCM (3×50 ml). The combined DCM extracts were dried over MgSO4, filtered washed with DCM and concentrated in vacuo to give the title compound (3.1 g, 70%) as a pale yellow oil.

Workup

  1. customThe reaction was quenched with water (100 ml)
  2. extractionextracted with DCM (3×50 ml)
  3. dry with materialThe combined DCM extracts were dried over MgSO4
  4. filtrationfiltered
  5. washwashed with DCM
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bdfbbffa22334f48a392536112661ea1
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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