Ethylenediamine → HCID 15329237, compound

HRID 2045826Notes

Reaction equation

HRID 2045826 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=O)=O)=[CH:4][CH:3]=1.[CH2:15]([NH2:18])[CH2:16][NH2:17]>C1(C)C(C)=CC=CC=1.C(Cl)Cl.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]23[CH2:8][CH2:9][C:10](=[O:12])[N:17]2[CH2:16][CH2:15][NH:18]3)=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 3301EthylenediamineHCID 776043-(4-Chlorobenzoyl)propionic acid

Product 1

HCID 15329237HCID 15329237, compoundYield 81.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 6344DichloromethaneSolventHCID 7237O-XyleneSolvent

Procedure

To a solution of 3-(4-chlorobenzoyl)propionic acid (40 g, 190 mmol) in xylene (250 mL) were added ethylenediamine (22.6 g, 376 mol), and 12M hydrochloric acid (0.500 mL, 6 mmol). The reaction mixture was stirred at reflux under Dean-Stark for 12 h, and cooled to RT. The solid was collected by filtration and washed with xylene to give the crude residue. This was dissolved in DCM (400 ml) and filtered. The filtrate was concentrated in vacuo to give 36.6 g (62%) of the racemic title compound as a beige solid.

Workup

  1. temperatureat reflux under Dean-Stark for 12 h
  2. filtrationThe solid was collected by filtration
  3. washwashed with xylene
  4. customto give the crude residue
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-35e252ac95604548b63c8d2d8704483e
Source dataset
uspto-grants-2013_11
Patent number
US08592403B2

Reaction notes

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