Triethylamine → HCID 8023320, compound

HRID 1814434Notes

Reaction equation

HRID 1814434 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][NH2:21])=[CH:15][CH:14]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C.O>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][NH:21][C:9](=[O:11])[CH2:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:15][CH:14]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 15880(4-Chlorophenyl)acetic acidHCID 674302-(4-Chlorophenyl)ethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 8023320HCID 8023320, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-chlorophenylacetic acid (500 mg, 3.0 mmol) and 2-(4-chlorophenyl)ethylamine (456 mg, 3.0 mmol) in DMF (50 ml) were added WSC.HCl (592 mg, 3.1 mmol), HOBt.H2O (474 mg, 3.1 mmol) and triethylamine (0.43 ml, 3.1 mmol), and the mixture was stirred at RT for 18 h. After adding water, the mixture was extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, and filtered. Concentrating under vacuum gave N-[2-(4-chlorophenyl)ethyl]-(4-chlorophenyl)acetamide (819 mg, 89%) which was used in the next step without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationConcentrating under vacuum

Sources & evidence

ORD record
ord-74417de8d49c424b8b4a4c6e0dcfae30
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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