Benzoyl chloride → HCID 46673126, compound

HRID 492985Notes

Reaction equation

HRID 492985 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 then triethylamine (8.25 ml) and benzoyl chloride (3.44 ml) were added thereto while cooling in an ice water bath, followed by warming to room temperature and stirring for 4 hrs. The reaction mixture was partitioned between ethyl acetate (200 ml) and a saturated aqueous solution of sodium hydrogencarbonate (100 ml). The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (100 ml), water (100 ml), brine (100 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated to provide the titled compound (8.19 g, quant.) as a colorless oil.

Workup

  1. temperaturewhile cooling in an ice water bath
  2. customThe reaction mixture was partitioned between ethyl acetate (200 ml)
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (100 ml), water (100 ml), brine (100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b79b88e999514b578eba6a8200b055e2
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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