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

HRID 407923Notes

Reaction equation

HRID 407923 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-9fe49ef74cc0440a9dbe6bb062925e68
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

Loading…