Benzoyl chloride → HCID 46673126, compound

HRID 2265589Notes

Reaction equation

HRID 2265589 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) were added thereto while stirring in an ice water bath. The reaction mixture was allowed to warm up to room temperature and stirred for 4 hr. 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 removed under reduced pressure to provide the titled compound as a colorless oil (8.19 g, quantitative).

Workup

  1. stirringstirred for 4 hr
  2. customThe reaction mixture was partitioned between ethyl acetate (200 ml)
  3. washThe separated organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (100 ml), water (100 ml) and brine (100 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c93ecfa422db49b5a86abc3ac84fb26f
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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