Water → HCID 68729916, compound

HRID 2065758Notes

Reaction equation

HRID 2065758 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][NH:10][CH2:9][CH2:8][N:7]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([S:34](Cl)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1.O>CN(C=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][N:10]([S:34]([C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([O:27][CH3:26])[CH:29]=2)(=[O:36])=[O:35])[CH2:9][CH2:8][N:7]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27375043-Methoxybenzenesulfonyl chlorideHCID 10682021Ethyl 1-benzylpiperazine-2-carboxylate

Product 1

HCID 68729916HCID 68729916, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-benzyl-piperazine-2-carboxylic acid ethyl ester (300 mg) in DMF (13 mL) was treated with triethylamine (0.5 mL) and 3-methoxybenzene sulfonyl chloride (274.6 mg) at RT for 2 hours. Water was added, and the inorganic layer was extracted with ethyl acetate (×3). The combined organic layers were dried (Na2SO4), filtered and evaporated to yield 1-benzyl-4-(3-methoxy-benzenesulfonyl)-piperazine-2-carboxylic acid ethyl ester as a colorless oil (417 mg), MS: 419.3 ([M+H]+).

Workup

  1. extractionthe inorganic layer was extracted with ethyl acetate (×3)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-0c648ddc0767433e97bc63a0ecd86b93
Source dataset
uspto-grants-2012_10
Patent number
US08288541B2

Reaction notes

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