Triethylamine → 4-[3-(Benzhydryl-sulfamoyl)-propyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1894367Notes

Reaction equation

HRID 1894367 reaction equation
[CH:1]([NH:14][S:15]([CH2:18][CH2:19][CH2:20]Cl)(=[O:17])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(N(CC)CC)C>CN(C)C=O>[C:25]([O:24][C:22]([N:29]1[CH2:34][CH2:33][N:32]([CH2:20][CH2:19][CH2:18][S:15](=[O:17])(=[O:16])[NH:14][CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:31][CH2:30]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 436538363-Chloro-propane-1-sulfonic acid benzhydryl-amide

Product 1

HCID 672053494-[3-(Benzhydryl-sulfamoyl)-propyl]-piperazine-1-carboxylic acid tert-butyl esterYield 52.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

In a three-neck round bottom flask equipped with argon inlet was charged with anhydrous dimethylformamide and 3-chloro-propane-1-sulfonic acid benzhydryl-amide (893 mg, 2.76 mmol). 1-Boc-piperazine (771 mg, 4.14 mmol, Aldrich) was added, followed by triethylamine (0.77 mL, 5.52 mmol). The mixture was stirred at 60° C. overnight. It was then heated at 120° C. for 10 min and at 180° C. for 15 min using the microwave synthesizer. Upon cooling, the reaction mixture was concentrated, and the residue was diluted with ethyl acetate. The organic layer was washed with water, brine, and concentrated. Purification of the crude residue by flash column chromatography gave 4-[3-(benzhydryl-sulfamoyl)-propyl]-piperazine-1-carboxylic acid tert-butyl ester as yellow oil (688 mg).

Workup

  1. customIn a three-neck round bottom flask equipped with argon inlet
  2. temperatureIt was then heated at 120° C. for 10 min and at 180° C. for 15 min
  3. temperatureUpon cooling
  4. concentrationthe reaction mixture was concentrated
  5. additionthe residue was diluted with ethyl acetate
  6. washThe organic layer was washed with water, brine
  7. concentrationconcentrated
  8. customPurification of the crude residue by flash column chromatography

Sources & evidence

ORD record
ord-737c2672e4fc4d93b43fc158d42b3cd8
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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