1,2-Dichloroethane → Ethyl Piperazine-2-carboxylate

HRID 497142Notes

Reaction equation

HRID 497142 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][N:10](C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:9][CH2:8][NH:7]1)=[O:5])[CH3:2].C1(C(C2C=CC=CC=2)CC(O)=O)C=CC=CC=1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][NH:10][CH2:9][CH2:8][NH:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 64798Diphenylpropionic acidHCID 142302694-Benzhydryl-piperazine-2-carboxylic acid ethyl ester

Product 1

HCID 10633257Ethyl Piperazine-2-carboxylateYield 73%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-Benzhydryl-piperazine-2-carboxylic acid ethyl ester (0.5 g, 1.54 mmol) in dry CH2Cl2 (25 ml) was added 3,3-diphenylpropanoic acid (0.35 g, 1.54 mmol) under nitrogen. To the reaction was added EDC (0.59 g, 3.08 mmol) and DMAP (cat) and the reaction mixture stirred under nitrogen at room temperature overnight. The reaction was then concentrated under reduced pressure. The residue dissolved in ethyl acetate: water (10:1) (100 ml). The organic was washed with water (20 ml, 2×) and 10% NaOH (20 ml) and dried over MgSO4 and evaporated to dryness. The resulting residue was purified by column chromatography using hexane: ethyl acetate (3:1) to give title compound in 73% yield.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. dissolutionThe residue dissolved in ethyl acetate: water (10:1) (100 ml)
  3. washThe organic was washed with water (20 ml, 2×) and 10% NaOH (20 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-c58f5ac3ecb443d783524c961cd55c6b
Source dataset
uspto-grants-2005_09
Patent number
US06949554B2

Reaction notes

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