Benzenepropanoic acid → HCID 4228842, compound

HRID 704408Notes

Reaction equation

HRID 704408 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:29]1([CH2:35][CH2:36][C:37](O)=[O:38])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1>[CH2:16]([N:23]1[CH2:28][CH2:27][N:26]([C:37](=[O:38])[CH2:36][CH2:35][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 107Benzenepropanoic acidHCID 10868DicyclohexylcarbodiimideHCID 759941-Benzylpiperazine

Product 1

HCID 4228842HCID 4228842, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dicyclohexylcarbodiimide (4.5 g) was added to a mixture of 3.52 g of 1-benzylpiperazine, 3.5 g of 3-phenylpropionic acid and 20 ml of tetrahydrofuran, and the mixture was stirred overnight at room temperature. The resultant dicyclohexylurea was filtered off, and the mother liquor was concentrated under reduced pressure. Ethyl acetate (100 ml) and 50 ml of water were added to the residue, and the mixture was made alkaline with potassium carbonate and then allowed to undergo phase separation. The ethyl acetate layer was washed in sequence with water and saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 6 g of 1-benzyl-4-(3-phenylpropionyl)piperazine.

Workup

  1. filtrationThe resultant dicyclohexylurea was filtered off
  2. concentrationthe mother liquor was concentrated under reduced pressure
  3. additionEthyl acetate (100 ml) and 50 ml of water were added to the residue
  4. customphase separation
  5. washThe ethyl acetate layer was washed in sequence with water and saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-be7d3404621146bd853702aed32c0eb1
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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