Triethylamine → HCID 28801055, compound

HRID 1411336Notes

Reaction equation

HRID 1411336 reaction equation
[N:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH:23]1([C:26](Cl)=[O:27])[CH2:25][CH2:24]1>ClCCl>[CH:23]1([C:26]([N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[CH:14][CH:15]=3)[CH2:6][CH2:5]2)=[O:27])[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 11804774-(piperazin-1-yl)benzoic acid

Product 1

HCID 28801055HCID 28801055, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-piperazin-1-yl-benzoic acid (20 g, 71.6 mmol) and triethylamine (58 g, 573 mmol) in dichloromethane (500 mL) was added cyclopropanecarbonyl chloride dropwise at 0° C. The reaction mixture was stirred at RT overnight. The solvent was removed by rotary evaporation. The residue was diluted with water, treated with sodium hydroxide, and washed with ethyl acetate and dichloromethane. The aqueous phase was acidified to pH 6 with 5 N HCl. The resulting precipitate was collected by filtration and concentrated to dryness to provide the title compound (10 g, 51% yield) as a white solid. 1H NMR(CH3OD, 400 MHz) δ (ppm) 7.87 (m, 2H), 6.95 (m, 2H), 3.90 (s, 2H), 3.73 (s, 2H), 3.29 (m, 4H), 1.99 (m, 1H), 0.86 (m, 4H).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. additionThe residue was diluted with water
  3. additiontreated with sodium hydroxide
  4. washwashed with ethyl acetate and dichloromethane
  5. filtrationThe resulting precipitate was collected by filtration
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-36503104d00446ac91fe6cfb4a0c31c4
Source dataset
uspto-grants-2014_12
Patent number
US08921372B2

Reaction notes

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