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

HRID 1643479Notes

Reaction equation

HRID 1643479 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>C(Cl)Cl>[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

5

Reactant 3

HCID 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 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Piperidin-2-yl-methanol (60.77 mmol, 1 eq) was dissolved in methylene chloride (150 ml) and triethylamine (151.92 mmol, 2.5 eq) at 0° C. and a solution of 4-methoxy-2,6-dimethyl-benzenesulfonyl chloride (60.77 mmol, 1 eq) in methylene chloride (50 ml) was added dropwise at 0° C. The reaction solution was stirred at room temperature for 14 h. The reaction solution was then diluted with methylene chloride (200 ml) and the organic phase was washed with saturated sodium chloride solution (2×50 ml), dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (5-20% ethyl acetate in hexane). Yield: 63%

Workup

  1. washthe organic phase was washed with saturated sodium chloride solution (2×50 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (5-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1aad27a8e7e14d64aa09c98559229d9d
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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