Triethylamine → HCID 45328385, compound

HRID 643248Notes

Reaction equation

HRID 643248 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].CCN(CC)CC.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>C(Cl)Cl>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([S:11]([C:3]2[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=2[Cl:1])[C:6]([OH:8])=[O:7])(=[O:13])=[O:12])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 756134-Chloro-3-(chlorosulphonyl)benzoic acidHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 45328385HCID 45328385, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-chloro-3-(chlorosulfonyl)benzoic acid (200 mg, 0.784 mmol) and Et3N (130 μl, 0.938 mmol) in CH2Cl2 (5 ml) was added 1-(t-butoxycarbonyl)piperazine (161 mg, 0.864 mmol) at 0° C. This mixture was stirred at room temperature overnight, and then diluted with CH2Cl2, washed with 10% citric acid solution. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated. The residue was suspended in Et2O, and the precipitate was collected by filtration to give crude 3-{[4-(tert-butoxycarbonyl)-1-piperazinyl]sulfonyl}-4-chlorobenzoic acid (200 mg, 63.0%).

Workup

  1. washwashed with 10% citric acid solution
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-0a369df24e3b4be98bc546f6b943fb81
Source dataset
uspto-grants-2010_04
Patent number
US07700586B2

Reaction notes

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