Chlorosulfonic acid → 4-(1-(2,2,2-Trifluoroacetyl)piperidin-4-yl)benzene-1-sulfonyl chloride

HRID 1715924Notes

Reaction equation

HRID 1715924 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]([F:23])([F:22])[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)=[O:9]>CCOC(C)=O>[F:23][C:7]([F:6])([F:22])[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)=[O:9]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 18348438HCID 18348438, compound

Product 1

HCID 179734784-(1-(2,2,2-Trifluoroacetyl)piperidin-4-yl)benzene-1-sulfonyl chlorideYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Chlorosulfonic acid (2 mL) was added to 2,2,2-trifluoro-1-(4-phenylpiperidin-1-yl)ethanone (1.0 g, 3.9 mmol) in a single portion, and the reaction was stirred for 20 minutes until gas evolution ceased (exothermic reaction). The solution was poured into a mixture of ice water (200 mL) and EtOAc (20 mL). The organic layer was concentrated and purified via silica gel chromatography using 8/2 hexanes/EtOAc to obtain 4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzene-1-sulfonyl chloride as a clear oil (1.3 g, 94%). 1H NMR (400 MHz, CDCl3) δ 8.02-8.00 (m, 2H), 7.48-7.45 (m, 2H), 4.78-4.73 (m, 1H), 4.19 (dd, J=14.0, 1.6 Hz, 1H), 3.32-3.25 (m, 1H), 3.02-2.86 (m, 2H), 2.03-2.02 (m, 2H), 1.81-1.70 (m, 2H).

Workup

  1. custom(exothermic reaction)
  2. concentrationThe organic layer was concentrated
  3. custompurified via silica gel chromatography

Sources & evidence

ORD record
ord-8c8d3d73ea95438eb6b2e78d7cb97457
Source dataset
uspto-grants-2010_09
Patent number
US07799822B2

Reaction notes

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