Methanesulfonyl chloride → Tert-butyl 4-(2-(methylsulfonamido)ethyl)piperazine-1-carboxylate

HRID 645776Notes

Reaction equation

HRID 645776 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][NH2:21])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]>N1C=CC=CC=1>[C:6]([O:10][C:11]([N:13]1[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][NH:21][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:17][CH2:18]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 1514400tert-Butyl 4-(2-aminoethyl)piperazine-1-carboxylate

Product 1

HCID 47215208Tert-butyl 4-(2-(methylsulfonamido)ethyl)piperazine-1-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (0.7 mL, 9.0 mmol) was added to a cooled solution of 4-(2-amino-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (1.33 g, 5.8 mmol) in pyridine (25.0 mL). The reaction was stirred for 12 h and partitioned between partitioned between aqueous sodium bicarbonate and methylene chloride. The organic phase was washed with 1M hydrochloric acid, aqueous sodium bicarbonate, brine, dried over anhydrous magnesium sulfate and concentrated. Purification of the crude residue by flash chromatography over silica gel using 0-5% methanol in methylene chloride gave 4-(2-methanesulfonylamino-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (0.70 g, 70%).

Workup

  1. custompartitioned
  2. custombetween partitioned between aqueous sodium bicarbonate and methylene chloride
  3. washThe organic phase was washed with 1M hydrochloric acid, aqueous sodium bicarbonate, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customPurification of the crude residue by flash chromatography over silica gel using 0-5% methanol in methylene chloride

Sources & evidence

ORD record
ord-bcefdefdb3f6428c843d20fe551f97f5
Source dataset
uspto-grants-2010_04
Patent number
US07705007B2

Reaction notes

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