Chlorosulfonic acid → 2-(1-Ethylpiperidin-4-ylmethyl)-4-fluorobenzenesulfonyl chloride

HRID 928045Notes

Reaction equation

HRID 928045 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH2:5][CH2:4]1)[CH3:2].[Cl:17][S:18](O)(=[O:20])=[O:19]>ClCCCl>[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][C:10]2[CH:11]=[C:12]([F:16])[CH:13]=[CH:14][C:15]=2[S:18]([Cl:17])(=[O:20])=[O:19])[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 709836871-Ethyl-4-(3-fluorobenzyl)piperidine2×

Product 1

HCID 867133532-(1-Ethylpiperidin-4-ylmethyl)-4-fluorobenzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 1-ethyl-4-(3-fluorobenzyl)piperidine (Intermediate 179, 0.210 g) in DCE (1 mL) was added to chlorosulfonic acid (2 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 2 hours. The resultant mixture was added carefully to ice/water and extracted with DCM. The organic layer was dried (Na2SO4) and filtered and the filtrate was evaporated to dryness to give 2-(1-ethylpiperidin-4-ylmethyl)-4-fluorobenzenesulfonyl chloride (0.290 g) as a solid.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-18635b4e8f464bbd96380c38b79304d2
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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