Dichloromethane → Butyl 4-(methylsulfonamido)piperidine-1-carboxylate

HRID 1844862Notes

Reaction equation

HRID 1844862 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:9])[CH2:4][CH2:3]1.[CH3:15][S:16](Cl)(=[O:18])=[O:17].CCN(C(C)C)C(C)C.ClCCl>O>[CH3:15][S:16]([NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:9])[CH2:6][CH2:7]1)(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 23025360HCID 23025360, compound

Product 1

HCID 86700931Butyl 4-(methylsulfonamido)piperidine-1-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a dried reaction flask, butyl 4-aminopiperidine-1-carboxylate (2.0 g, 10.0 mmol), methanesulfonyl chloride (0.77 mL, 10 mmol), and DIEA (2.6 mL, 15 mmol) were added to dichloromethane (40 mL). The mixture was stirred under an ice-water bath for 2 hr. LC-MS showed that the product was formed and the reactants vanished. The solution was concentrated under reduced pressure to produce a yellow oil. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate, and was purified with silica-gel column chromatography (ethyl acetate:petroleum ether=1:2) to obtain a white solid (2.67 g) in 96.0% yield.

Workup

  1. customwas formed
  2. concentrationThe solution was concentrated under reduced pressure
  3. customto produce a yellow oil
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customwas purified with silica-gel column chromatography (ethyl acetate:petroleum ether=1:2)

Sources & evidence

ORD record
ord-c7aa5ea2f5b54b7196d7925e5472c681
Source dataset
uspto-grants-2015_02
Patent number
US08946279B2

Reaction notes

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