p-Aminoacetophenone → N-(4-acetylphenyl)-3-(piperidin-1-ylsulfonyl)benzamide

HRID 1967508Notes

Reaction equation

HRID 1967508 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[N:44]1([S:50]([C:53]2[CH:54]=[C:55]([CH:59]=[CH:60][CH:61]=2)[C:56](O)=[O:57])(=[O:52])=[O:51])[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1>C(OCC)(=O)C.CN(C=O)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:56](=[O:57])[C:55]2[CH:59]=[CH:60][CH:61]=[C:53]([S:50]([N:44]3[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]3)(=[O:52])=[O:51])[CH:54]=2)=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

Participants

7

Reactant 4

HCID 7468p-AminoacetophenoneHCID 81531DiisopropylethylamineHCID 7678893-(Piperidine-1-sulfonyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 1127074N-(4-acetylphenyl)-3-(piperidin-1-ylsulfonyl)benzamideYield 41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(4-aminophenyl)ethanone (151 mg), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (565 mg) and N,N-diisopropylethylamine (0.39 mL) were added in that order to a DMF (4.0 mL) solution of 3-(piperidin-1-ylsulfonyl)benzoic acid (200 mg), and stirred at room temperature for 2 hours. Ethyl acetate was added to the reaction liquid, washed three times with water, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 80%, gradient) to give the entitled compound (117 mg, 41%) as a white crystal.

Workup

  1. washwashed three times with water
  2. dry with materialdried with sodium sulfate
  3. customThe drying agent was removed through filtration
  4. customthe solvent was evaporated off under reduced pressure
  5. customThe residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 80%, gradient)

Sources & evidence

ORD record
ord-a3463debc68e46f08037a3f1ab9f3cec
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

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