Water → HCID 55266256, compound

HRID 1174519Notes

Reaction equation

HRID 1174519 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH3:8])[CH2:3]1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18].O>ClCCl.CS(Cl)(=O)=O>[CH3:8][N:4]1[CH2:5][CH2:6][CH2:7][CH:2]([O:1][S:17]([CH3:16])(=[O:19])=[O:18])[CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 980163-Piperidinol, 1-methyl-

Product 1

HCID 55266256HCID 55266256, compoundYield 325.1%

Reagents, catalysts & solvents 2

HCID 31297Methanesulfonyl chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxy-N-methyl piperidine (2 cm3, 17.4 mmol) in dichloromethane (40 cm3) was added triethylamine (3.6 cm3, 26.05 mmol) and then methanesulfonyl chloride (1.5 cm3, 19:1 mmol). The reaction was then stirred for 3 h before a further aliquot (0.2 equiv., 3.47 mmol) of methanesulfonyl chloride was added. Stirring was continued for another 2 h at room temperature before the reaction was treated with water (60 cm3) and extracted into dichloromethane (40 cm3). The organic layer was washed with saturated aqueous sodium chloride solution (60 cm3) and dried over sodium sulfate before being evaporated under reduced pressure to afford (A) (2.18 g, 11.28 mmol, 65%).

Workup

  1. additionwas added
  2. extractionextracted into dichloromethane (40 cm3)
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution (60 cm3)
  4. dry with materialdried over sodium sulfate
  5. custombefore being evaporated under reduced pressure

Sources & evidence

ORD record
ord-dbec53f4337a411aa8cc0d5a4fd55cf7
Source dataset
uspto-grants-2010_11
Patent number
US07838518B2

Reaction notes

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