Methanesulfonyl chloride → HCID 59527259, compound

HRID 384463Notes

Reaction equation

HRID 384463 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:21]=[CH:22][CH:23]=1)[O:13][CH2:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:21]=[CH:22][CH:23]=1)[O:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([S:34]([CH3:33])(=[O:36])=[O:35])[CH2:17][CH2:16]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 68509956HCID 68509956, compound

Product 1

HCID 59527259HCID 59527259, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-{[3-(Benzyloxy)phenoxy]methyl}piperidine hydrochloride (1.5 g) was dissolved in chloroform (30 mL), and diisopropyl ethylamine (3.13 mL) and methanesulfonyl chloride (0.52 mL) were added thereto under ice-cooling, followed by stirring at room temperature for 2 hours. Saturated aqueous sodium bicarbonate solution was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was powdered and purified from chloroform/hexane to obtain 4-{[3-(benzyloxy)phenoxy]methyl}-1-(methylsulfonyl)piperidine (1.508 g).

Workup

  1. temperatureunder ice-cooling
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. custompurified from chloroform/hexane

Sources & evidence

ORD record
ord-552f4408178547e098ef8d424ee8f97d
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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