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

HRID 852095Notes

Reaction equation

HRID 852095 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[N:12]1([CH2:18][CH2:19][CH2:20][OH:21])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(N(CC)CC)C>ClCCl>[N:12]1([CH2:18][CH2:19][CH2:20][O:21][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 66032Piperidine-1-propanol

Product 1

HCID 179446593-(Piperidin-1-yl)propyl 4-methylbenzene-1-sulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add p-toluenesulfonyl-chloride (1.33 g, 6.98 mmol), portionwise, to a mixture of 3-piperidin-1-yl-propan-1-ol (1 g, 6.98 mmol), triethylamine (1.41 g, 13.9 mmol) and dichloromethane (6 mL). Stir the resulting suspension vigorously overnight at room temperature. Add water, separate the organic layer, and extract the aqueous layer with dichloromethane, twice. Combine the organic layers and wash with water, dry with sodium sulfate and evaporate the solvent to give the final, desired compound. The final compound may be purified by chromatography.

Workup

  1. customAdd water, separate the organic layer
  2. extractionextract the aqueous layer with dichloromethane
  3. washwash with water
  4. dry with materialdry with sodium sulfate
  5. customevaporate the solvent

Sources & evidence

ORD record
ord-2986eb574c3145e09bbe427c70fa64dc
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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