Hydrochloric Acid → Methyl 2-((4,4-difluorocyclohexyl)methyl)-isonicotinate hydrochloride

HRID 1963254Notes

Reaction equation

HRID 1963254 reaction equation
[F:1][C:2]1([F:19])[CH2:7][CH2:6][CH:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH2:4][CH2:3]1.[ClH:20]>>[ClH:20].[F:19][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 66732474HCID 66732474, compound

Product 1

HCID 66732496Methyl 2-((4,4-difluorocyclohexyl)methyl)-isonicotinate hydrochloride

Procedure

Methyl 2-((4,4-difluorocyclohexyl)methyl)isonicotinate (5 g, 18.6 mmol) was treated with HCl (4 M in dioxane) and evaporated to give methyl 2-((4,4-difluorocyclohexyl)methyl)-isonicotinate hydrochloride (5.6 g, 18.32 mmol) which was dissolved in MeOH (100 mL), then platinum(IV) oxide (0.416 g, 1.83 mmol) was added. The mixture was hydrogenated in a Büchi hydrogenator at 5 bar overnight. The catalyst was filtered off and solvents were evaporated yielding methyl 2-((4,4-difluorocyclohexyl)methyl)piperidine-4-carboxylate hydrochloride (5.1 g, 89%). MS m/z 276 (M+H)+

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-85769754428e462a9d030d2449411294
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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