Water → HCID 57993617, compound

HRID 388781Notes

Reaction equation

HRID 388781 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:6][CH2:5]1.CCN(C(C)C)C(C)C.[CH:28]1([S:31](Cl)(=[O:33])=[O:32])[CH2:30][CH2:29]1.O>C(Cl)Cl>[CH:28]1([S:31]([NH:1][CH2:2][CH2:3][N:4]2[CH2:9][CH2:8][CH:7]([CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH2:6][CH2:5]2)(=[O:33])=[O:32])[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 34178247tert-Butyl {[1-(2-aminoethyl)piperidin-4-yl]methyl}carbamate

Product 1

HCID 57993617HCID 57993617, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 15° C., to a solution of tert-butyl (1-(2-aminoethyl)piperidin-4-yl)methylcarbamate (2.00 g, 7.78 mmol) and DIPEA (3.00 g, 23.3 mmol) in CH2Cl2 (40 mL) was added slowly cyclopropylsulfonyl chloride (3.40 g, 25.0 mmol) under Ar. The reaction mixture was stirred at room temperature for 2 hrs. Water (30 mL) was added, and the mixture was extracted with CH2Cl2 (3×30 mL). The combined extract was washed with saturated NaHCO3 (40 mL) and dried over anhydrous Na2SO4. After filtration the solvent was removed in vacuo, and the residue was applied to flash column chromatography (3-7% CH3OH in CH2Cl2) to provide tert-butyl (1-(2-(cyclopropanesulfonamido)ethyl)piperidin-4-yl)methylcarbamate as pale yellow oil (2.2 g, 78%).

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×30 mL)
  2. extractionThe combined extract
  3. washwas washed with saturated NaHCO3 (40 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed in vacuo

Sources & evidence

ORD record
ord-39c1750959fd458887d5e6e2abefd516
Source dataset
uspto-grants-2013_02
Patent number
US08377968B2

Reaction notes

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