Hydrochloric Acid → [1-(4-Methoxy-2,6-dimethyl-phenylsulfonyl)-piperidin-2-yl]-methanol

HRID 2059881Notes

Reaction equation

HRID 2059881 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][OH:8].C(N(CC)CC)C.[CH3:16][O:17][C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([S:25](Cl)(=[O:27])=[O:26])=[C:20]([CH3:29])[CH:19]=1.Cl>ClCCl>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH3:29])[C:21]([S:25]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]2[CH2:7][OH:8])(=[O:26])=[O:27])=[C:22]([CH3:24])[CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 94263Piperidin-2-ylmethanolHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride

Product 1

HCID 43574491[1-(4-Methoxy-2,6-dimethyl-phenylsulfonyl)-piperidin-2-yl]-methanolYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Piperidin-2-ylmethanol (1.1 eq) was dissolved in dichloromethane (4 ml/mmol), cooled, and triethylamine (2.5 eq) was added. A solution of 4-methoxy-2,6-dimethylbenzenesulfonyl chloride (1 eq) in dichloromethane (2 ml/mmol) was added dropwise at 0° C., then the mixture was stirred for 90 min at room temperature. Hydrogen chloride solution (eq, 0.5 mol/l, 2 ml/mmol) was added, the mixture stirred for 15 min and the phases separated. The organic phase was washed with water, dried over sodium sulfate and concentrated to small volume under vacuum. The crude product was used in the next stage with no further purification. Yield: 20%

Workup

  1. temperaturecooled
  2. stirringthe mixture stirred for 15 min
  3. customthe phases separated
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to small volume under vacuum
  7. customThe crude product was used in the next stage with no further purification

Sources & evidence

ORD record
ord-494a1fc12f3a418c85ebe7ff4ed62c1c
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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