Triethylamine → HCID 9952791, compound

HRID 1109471Notes

Reaction equation

HRID 1109471 reaction equation
C(N(CC)CC)C.C(OC(Cl)=O)C.[C:14]([NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=1)(=[O:17])[CH2:15][CH3:16].[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[CH:31][CH:30]=1>CN(C)C=O.C(Cl)Cl>[C:14]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([N:40]2[CH2:39][CH2:38][N:37]([CH2:36][CH2:35][C:32]3[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=3)[CH2:42][CH2:41]2)=[O:25])=[CH:26][CH:27]=1)(=[O:17])[CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 47779524-(propionylamino)benzoic acidHCID 122357141-[2-(4-Chlorophenyl)ethyl]piperazine

Product 1

HCID 9952791HCID 9952791, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 6344DichloromethaneSolvent

Procedure

A solution of 2 g of triethylamine in 5 ml of anhydrous dimethylformamide and then a solution of 2.15 g of chloroformic acid ethyl ester in 10 ml of methylene chloride is added dropwise to a solution, stirred at from -5° to 0°, of 3.8 g of p-propionamidobenzoic acid in 30 ml of anhydrous dimethylformamide. The reaction mixture is stirred for 30 minutes at from 0° to 5° and then a solution of 4.4 g of 1-[2-(4-chlorophenyl)ethyl]-piperazine in 25 ml of anhydrous dimethylformamide is added dropwise thereto. The suspension is stirred overnight at approximately 5° and concentrated by evaporation. 50 ml of water are added to the residue and the solution is rendered alkaline with 2N sodium hydroxide solution and extracted by shaking with methylene chloride. The combined organic phases are washed with water, dried over sodium sulfate, filtered and concentrated by evaporation. The residue is chromatographed over silica gel and the resulting oil is crystallised from acetone/diethyl ether, yielding 1-[4-(N-propionylamino)-benzoyl]-4-[2-(4-chlorophenyl)ethyl]-piperazine having a melting point of 131°-132°.

Workup

  1. stirringThe suspension is stirred overnight at approximately 5°
  2. concentrationconcentrated by evaporation
  3. addition50 ml of water are added to the residue
  4. extractionextracted
  5. stirringby shaking with methylene chloride
  6. washThe combined organic phases are washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation
  10. customThe residue is chromatographed over silica gel
  11. customthe resulting oil is crystallised from acetone/diethyl ether

Sources & evidence

ORD record
ord-d0346b035db4463f8ea27742ef96c973
Source dataset
uspto-grants-1994_06
Patent number
US05321027

Reaction notes

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