Hydrochloric Acid → (S)-3-(3-chloro-5-(trifluoromethyl)pyridin-2-ylamino)-1,4'-bipiperidin-2-one hydrochloride

HRID 407970Notes

Reaction equation

HRID 407970 reaction equation
[Cl:1][C:2]1[C:3]([NH:12][C@H:13]2[CH2:18][CH2:17][CH2:16][N:15]([CH:19]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)[C:14]2=[O:32])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(Cl)Cl.Cl>CO>[ClH:1].[Cl:1][C:2]1[C:3]([NH:12][C@H:13]2[CH2:18][CH2:17][CH2:16][N:15]([CH:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)[C:14]2=[O:32])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 67470467(S)-tert-butyl 3-(3-chloro-5-(trifluoromethyl)pyridin-2-ylamino)-2-oxo-1,4'-bipiperidine-1'-carboxylate

Product 1

HCID 67470474(S)-3-(3-chloro-5-(trifluoromethyl)pyridin-2-ylamino)-1,4'-bipiperidin-2-one hydrochlorideYield 176%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A flask was charged with (S)-tert-butyl 3-(3-chloro-5-(trifluoromethyl)pyridin-2-ylamino)-2-oxo-1,4′-bipiperidine-1′-carboxylate (0.51 g, 1.1 mmol), DCM (10 mL), methanol (1 mL), and HCl (2.7 mL, 11 mmol) (in dioxane). The reaction mixture was stirred at ambient temperature overnight. The organic solvents were removed under reduced pressure to provide (S)-3-(3-chloro-5-(trifluoromethyl)pyridin-2-ylamino)-[1,4′-bipiperidin]-2-one hydrochloride (0.40 g, 91% yield). Mass spectrum (apci) m/z=377.2 (M+H).

Workup

  1. customThe organic solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-a5ad5ee497d24bd2bb082d839406a5c3
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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