4-Toluenesulfonyl chloride → HCID 14577395, compound

HRID 1110769Notes

Reaction equation

HRID 1110769 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][C:13]1[CH:14]=[C:15]([CH:26]=[CH:27][CH:28]=1)[C:16]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][OH:25])[CH2:20][CH2:19]1)=[O:17]>N1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:25][CH2:24][CH:21]2[CH2:22][CH2:23][N:18]([C:16](=[O:17])[C:15]3[CH:26]=[CH:27][CH:28]=[C:13]([CH3:12])[CH:14]=3)[CH2:19][CH2:20]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 14577394HCID 14577394, compound

Product 1

HCID 14577395HCID 14577395, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
20 °C

Procedure

53.3 g (0.28 mol) of 4-methylbenzenesulphonyl chloride in 60 ml of pyridine are added to a solution of 52 g (0.22 mol) of 1-(3-methylbenzoyl)-4-piperidinemethanol in 100 ml of pyridine. The mixture is stirred at 20° C. for 4 h, and then poured into ice. The aqueous phase is extracted with dichloromethane, and the organic phase washed with 10 N aqueous hydrochloric acid solution and dried over magnesium sulphate. The solvents are evaporated off under reduced pressure and 70 g of white solid are obtained.

Workup

  1. additionpoured into ice
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. washthe organic phase washed with 10 N aqueous hydrochloric acid solution
  4. dry with materialdried over magnesium sulphate
  5. customThe solvents are evaporated off under reduced pressure and 70 g of white solid
  6. customare obtained

Sources & evidence

ORD record
ord-6f0c4eb7be254193bce0f191fbfd2024
Source dataset
uspto-grants-1990_12
Patent number
US04977159

Reaction notes

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