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

HRID 1643471Notes

Reaction equation

HRID 1643471 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([S:17](Cl)(=[O:19])=[O:18])=[C:12]([CH3:21])[CH:11]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[CH2:28][OH:29]>>[CH3:8][O:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([S:17]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]2[CH2:28][OH:29])(=[O:19])=[O:18])=[C:12]([CH3:21])[CH:11]=1

Participants

4

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]-methanol

Conditions

Temperature
0 °C

Procedure

A solution of triethylamine (2.5 eq) and 4-methoxy-2,6-dimethylbenzenesulfonyl chloride (13.04 mmol, 1 eq) in MC (10 ml) was added dropwise to a solution of piperidin-2-ylmethanol (13.04 mmol) in MC (30 ml) at 0° C. and the mixture was stirred at 0° C. for 30 min. It was then stirred at room temperature for 14 h, MC (50 ml) was subsequently added to the mixture and the mixture was washed with water and sat. sodium chloride solution. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude product obtained in this way was purified by column chromatography. Yield: 3.2 g (79%)

Workup

  1. stirringIt was then stirred at room temperature for 14 h
  2. additionMC (50 ml) was subsequently added to the mixture
  3. washthe mixture was washed with water and sat. sodium chloride solution
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-08474fc324b94ea095e7c9a0872e0716
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

Loading…