4-Toluenesulfonyl chloride → 3-(Piperidin-1-yl)propyl 4-methylbenzene-1-sulfonate

HRID 1667746Notes

Reaction equation

HRID 1667746 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[N:1]1([CH2:7][CH2:8][CH2:9][O:10][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=2)(=[O:19])=[O:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 66032Piperidine-1-propanol

Product 1

HCID 179446593-(Piperidin-1-yl)propyl 4-methylbenzene-1-sulfonateYield 64.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a mixture of 0.286 g (2 mmole) of 3-piperidin-1-yl-propan-1-ol, and 2 mL of pyridine was added 0.001 g of 4-dimethylaminopyridine and 0.381 g (2 mmole) of p-toluenesulphonyl chloride. The mixture was stirred at ambient temperature overnight and then concentrated under reduced pressure. The residue was taken up in 20 mL of dichloromethane and washed once with 10 mL of saturated sodium bicarbonate, twice with 10 mL of water, and then brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.384 g of toluene-4-sulfonic acid 3-piperidin-1-yl-propyl ester as a pink solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed once with 10 mL of saturated sodium bicarbonate, twice with 10 mL of water
  3. dry with materialbrine, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-77f378ada5574d72a43764ca204d5005
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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