Ethylenediamine → HCID 22909780, compound

HRID 1379166Notes

Reaction equation

HRID 1379166 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:27])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23]Br)=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C(=O)([O-])[O-].[K+].[K+].[CH2:34]([NH2:37])[CH2:35][NH2:36]>CS(C)=O.ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:27])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][NH:36][CH2:35][CH2:34][NH2:37])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 22909785HCID 22909785, compound

Product 1

HCID 22909780HCID 22909780, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

0.35 g (0.81 mmol) of N-{3-(3,4-dimethylphenyl)propyl}-4-(2-bromoethoxy)-3-methoxyphenylacetamide obtained in step 1 of Example 2 was dissolved in 3 ml of dimethylsulfoxide and 0.56 g (4.02 mmol) of potassium carbonate was added thereto. To this mixture, 0.48 g (8.06 mmol) of ethylenediamine was slowly added at room temperature, followed by stirring at room temperature for 4 hours. The reaction mixture was diluted with 40 ml of dichloromethane, washed with water and acidified with 1N HCl and the aqueous layer was separated. The aqueous layer was basified with hydrogen peroxide, extracted with 40 ml of dichloromethane, dried and the solvent was removed under a reduced pressure. The residue was triturated with a mixture of dichloromethane and hexane(1:2) to obtain 0.10 g of the title compound as a white solid(yield: 30%).

Workup

  1. washwashed with water
  2. customthe aqueous layer was separated
  3. extractionextracted with 40 ml of dichloromethane
  4. customdried
  5. customthe solvent was removed under a reduced pressure
  6. customThe residue was triturated with a mixture of dichloromethane and hexane(1:2)

Sources & evidence

ORD record
ord-3bb7f86a32174dd6ba4246946859a574
Source dataset
uspto-grants-1997_09
Patent number
US05670546

Reaction notes

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