Hydrochloric Acid → (S)-3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-1,4'-bipiperidin-2-one hydrochloride

HRID 407929Notes

Reaction equation

HRID 407929 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[C:5]([F:12])=[CH:4][C:3]=1[NH:13][C@H:14]1[CH2:19][CH2:18][CH2:17][N:16]([CH:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)[C:15]1=[O:33].[ClH:34].O1CCOCC1>C(Cl)Cl.CO>[ClH:34].[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[C:5]([F:12])=[CH:4][C:3]=1[NH:13][C@H:14]1[CH2:19][CH2:18][CH2:17][N:16]([CH:20]2[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]2)[C:15]1=[O:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67470435(S)-tert-butyl 3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-2-oxo-1,4'-bipiperidine-1'-carboxylate

Product 1

HCID 66803298(S)-3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-1,4'-bipiperidin-2-one hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-tert-butyl 3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-2-oxo-1,4′-bipiperidine-1′-carboxylate (4.6 g, 9.4 mmol) was dissolved in CH2Cl2 (100 mL) and methanol (10 mL). 4N HCl in dioxane (24 mL, 94 mmol) was added and the reaction stirred at ambient temperature overnight. The reaction was concentrated to provide (S)-3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-1,4′-bipiperidin-2-one hydrochloride, which was used directly in the next step without purification.

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-f908cb5f9c904e72b923ad1164e78323
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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