Hydrochloric Acid → 3-(2-Fluoro-4-(methylsulfonyl)phenylamino)-1,4'-bipiperidin-2-one

HRID 407936Notes

Reaction equation

HRID 407936 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:12][CH:13]1[CH2:18][CH2:17][CH2:16][N:15]([CH:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)[C:14]1=[O:32].Cl.O1CCOCC1>C(Cl)Cl.CO>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:12][CH:13]1[CH2:18][CH2:17][CH2:16][N:15]([CH:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[C:14]1=[O:32]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66802697Tert-butyl 3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxo-1,4'-bipiperidine-1'-carboxylate

Product 1

HCID 674706263-(2-Fluoro-4-(methylsulfonyl)phenylamino)-1,4'-bipiperidin-2-oneYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxo-1,4′-bipiperidine-1′-carboxylate (7.9 g, 17 mmol) was dissolved in CH2Cl2 (100 mL) and MeOH (10 mL). 4N HCl in dioxane (29 mL, 118 mmol) was added and the reaction stirred at ambient temperature for 3 hours. The reaction was concentrated and purified over silica gel (50-100% EtOAc in hexanes followed by 5% ammoniated methanol in CH2Cl2) to afford 3-(2-fluoro-4-(methylsulfonyl)phenylamino)-1,4′-bipiperidin-2-one (6.2 g, 17 mmol, 100% yield) as yellow solid.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified over silica gel (50-100% EtOAc in hexanes followed by 5% ammoniated methanol in CH2Cl2)

Sources & evidence

ORD record
ord-4b24dc20a952475b88d4e18d76f718c8
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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