Benzoyl chloride → HCID 46673126, compound

HRID 1712638Notes

Reaction equation

HRID 1712638 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][N:7]1[CH2:8][CH2:9][N:10]([C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:11][CH2:12]1)[CH3:2]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 207112Ethyl piperazine-1-acetate

Product 1

HCID 46673126HCID 46673126, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(Ethoxycarbonylmethyl)piperazine (5.1 g) was dissolved in tetrahydrofuran (300 ml) under a nitrogen atmosphere, and triethylamine (8.25 ml) and benzoyl chloride (3.44 ml) was added thereto with cooling in an ice water bath. The reaction mixture was brought to room temperature, followed by stirring for 4 hours. The reaction mixture was partitioned between ethyl acetate (200 ml) and a saturated aqueous solution of sodium hydrogencarbonate (100 ml). The separated organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (100 ml), water (100 ml) and brine (100 ml), and dried over sodium sulfate. The solvent was distilled off under reduced pressure to give the title compound (8.19 g, quant.) as a colorless oil.

Workup

  1. temperaturewith cooling in an ice water bath
  2. customwas brought to room temperature
  3. customThe reaction mixture was partitioned between ethyl acetate (200 ml)
  4. washThe separated organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (100 ml), water (100 ml) and brine (100 ml)
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-aee5710dc47a40b9b448297e5ea135b8
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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