Formic Acid → Ordopidine

HRID 2358034Notes

Reaction equation

HRID 2358034 reaction equation
[CH2:1]([N:3]1[CH2:8][CH:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([S:15]([CH3:18])(=[O:17])=[O:16])[C:10]=2[F:19])[CH2:5][CH2:4]1)[CH3:2].C(O)=O>[Pd].C(O)(C)C>[CH2:1]([N:3]1[CH2:4][CH2:5][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([S:15]([CH3:18])(=[O:17])=[O:16])[C:10]=2[F:19])[CH2:7][CH2:8]1)[CH3:2]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 166553451-Ethyl-4-[2-fluoro-3-(methylsulfonyl)phenyl]-1,2,3,6-tetrahydropyridine

Product 1

HCID 11701939OrdopidineYield 175.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 1-ethyl-4-[2-fluoro-3-(methylsulfonyl)phenyl]-1,2,3,6-tetrahydropyridine (5 g, 17, 7 mmol), formic acid (3.4 ml, 90 mmol) and palladium on carbon (1.1 g) in isopropanol (50 ml) was shaken in a parr apparatus for 20 h. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated and evaporated to dryness. Aqueous sodium carbonate (10%, 200 ml) was added and the mixture was extracted with ethyl acetate (3×100 ml). The combined organic phases was dried (MgSO4) and evaporated to dryness. Flash column chromatography (ethylacetate/methanol, 1:1) gave the title compound (3.5 g, 70%). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 280.2° C. MS m/z (relative intensity, 70 eV) 285 (M+, 12), 270 (bp), 57 (19), 84 (15) 133 (9).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customevaporated to dryness
  4. additionAqueous sodium carbonate (10%, 200 ml) was added
  5. extractionthe mixture was extracted with ethyl acetate (3×100 ml)
  6. dry with materialThe combined organic phases was dried (MgSO4)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-7a6703414b324e3fbfa41a783d5e68cb
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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