Benzenesulfonyl chloride → HCID 86639803, compound

HRID 1804857Notes

Reaction equation

HRID 1804857 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][C:14]([CH2:18][CH2:19][OH:20])([OH:17])[CH2:13][CH2:12]1.[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1C=CC=CC=1>[C:21]1([S:27]([O:20][CH2:19][CH2:18][C:14]2([OH:17])[CH2:15][CH2:16][N:11]([C:3]3[CH:4]=[C:5]([O:9][CH3:10])[C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[CH2:12][CH2:13]2)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 68552870HCID 68552870, compound

Product 1

HCID 86639803HCID 86639803, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-(2,4-dichloro-5-methoxyphenyl)-4-(2-hydroxyethyl)piperidin-4-ol (500 mg, 1.561 mmol) in pyridine (2 mL) was cooled to 0° C. and then treated with benzenesulfonyl chloride (331 mg, 1.874 mmol). The reaction was stirred at RT for 1 h before being quenched with water. The resultant mixture was extracted with EtOAc. The organic phase was concentrated in vacuo, and the resultant residue was purified by flash chromatography using 0-30% EtOAc in hexanes as the eluent to give 2-(1-(2,4-dichloro-5-methoxyphenyl)-4-hydroxypiperidin-4-yl)ethyl benzenesulfonate (340 mg, 0.739 mmol, 47% yield) was obtained as a yellow oil.

Workup

  1. custombefore being quenched with water
  2. extractionThe resultant mixture was extracted with EtOAc
  3. concentrationThe organic phase was concentrated in vacuo
  4. customthe resultant residue was purified by flash chromatography

Sources & evidence

ORD record
ord-791035a209014ceaadcc5346155a7e20
Source dataset
uspto-grants-2013_01
Patent number
US08354432B2

Reaction notes

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