4-Toluenesulfonyl chloride → HCID 14577395, compound

HRID 1090100Notes

Reaction equation

HRID 1090100 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]([C:19]([N:21]2[CH2:26][CH2:25][CH:24]([CH2:27][OH:28])[CH2:23][CH2:22]2)=[O:20])[CH:16]=[CH:17][CH:18]=1>N1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:28][CH2:27][CH:24]2[CH2:23][CH2:22][N:21]([C:19]([C:15]3[CH:16]=[CH:17][CH:18]=[C:13]([CH3:12])[CH:14]=3)=[O:20])[CH2:26][CH2:25]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-methylphenylsulphonyl chloride in 60 ml of pyridine are added to a solution of 52 g (0.22 mol) of 1-[(3-methylphenyl)carbonyl]-4-piperidinemethanol in 100 ml of pyridine. The mixture is stirred at 20° C. for 4 h and then poured into ice. The phase is extracted with dichloromethane and the organic phase is washed with 10N 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. Melting point: 68°-70° C.

Workup

  1. additionpoured into ice
  2. extractionThe phase is extracted with dichloromethane
  3. washthe organic phase is washed with 10N 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-9e728a41a7604b97b7a3c4a280870fa9
Source dataset
uspto-grants-1992_01
Patent number
US05081128

Reaction notes

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