p-Anisoyl chloride → 1-(4-Methoxybenzoyl)-4-(4-but-2-ynyloxybenzenesulfonyl)piperidine-4-carboxylic acid methyl ester

HRID 353568Notes

Reaction equation

HRID 353568 reaction equation
[CH3:1][O:2][C:3]([C:5]1([S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[C:23][CH3:24])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].C(N(CC)CC)C.[CH3:32][O:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1.CN(C1C=CC=CN=1)C>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([S:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]#[C:23][CH3:24])=[CH:18][CH:19]=2)(=[O:13])=[O:12])[CH2:10][CH2:9][N:8]([C:38](=[O:39])[C:37]2[CH:41]=[CH:42][C:34]([O:33][CH3:32])=[CH:35][CH:36]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 54136994HCID 54136994, compound

Product 1

HCID 536440531-(4-Methoxybenzoyl)-4-(4-but-2-ynyloxybenzenesulfonyl)piperidine-4-carboxylic acid methyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-(4-but-2-ynyloxy-benzenesulfonyl)-piperidine-4-carboxylic acid methyl ester (260 mg, 0.77 mmol) in chloroform (7 ml) was added triethylamine (311 mg, 3.08 mmol), 4-methoxybenzoyl chloride (158 mg, 0.92 mmol) followed by a catalytic amount of dimethylaminopyridine. The resulting mixture was stirred for 15 hours at room temperature, quenched with water and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated to give 280 mg (75%) of the product as a solid. HR-MS: m/z Calculated for C25H27NO7S 486.1581; Found 486.1576.

Workup

  1. customquenched with water
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7516ab06f99a4c85a43fce928c189e44
Source dataset
uspto-grants-2004_06
Patent number
US06753337B2

Reaction notes

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