4-Toluenesulfonyl chloride → HCID 86642832, compound

HRID 1667737Notes

Reaction equation

HRID 1667737 reaction equation
[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>N1C=CC=CC=1>[N:1]1([CH2:7][CH2:8][O:9][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 18232N-Piperidinoethanol

Product 1

HCID 86642832HCID 86642832, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.573 g (4 mmole) of 2-piperidin-1-yl-ethanol and 8 mL of pyridine at 0 degrees was added 0.763 g (4 mmole) of p-toluenesulphonyl chloride. The mixture was stirred at ambient temperature for 3 hours. The mixture was concentrated under reduced pressure and 10 mL of water was added. The mixture was extracted twice with 10 mL of dichloromethane. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give toluene-4-sulfonic acid 2-piperidin-1-yl-ethyl ester as a purple oil, which was carried to next step without further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and 10 mL of water
  2. additionwas added
  3. extractionThe mixture was extracted twice with 10 mL of dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-241c925c3c94495fbe6c92def022800f
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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