Hydrochloric Acid → HCID 11702233, compound

HRID 2263488Notes

Reaction equation

HRID 2263488 reaction equation
[F:1][C:2]1[C:7]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[C:13]1[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH3:21])[CH2:17][CH:18]=1.Cl>[Pd].CO>[F:1][C:2]1[C:7]([O:8][C:9]([F:10])([F:11])[F:12])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:13]1[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH3:21])[CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57453799HCID 57453799, compound

Product 1

HCID 11702233HCID 11702233, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-[2-fluoro-3-(trifluoromethoxy)phenyl]-1-propyl-1,2,3,6-tetrahydro-pyridine (0.55 g, 1.8 mmol), palladium on carbon (0.09 g), hydrochloric acid (0.5 ml, conc), in methanol (30 ml) was hydrogenated at 50 psi for 15 h under hydrogen. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated and evaporated to dryness to give 0.55 g of crude product. Purification by flash column chromatography (Isooctane/ethylacetate, 1:1) gave the title compound 0.22 g (40%). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 221-222° C. MS m/z (relative intensity, 70 eV) 305 (M+, 3), 277 (14), 276 (bp), 233 (6) 193 (8).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customevaporated to dryness
  4. customto give 0.55 g of crude product
  5. customPurification by flash column chromatography (Isooctane/ethylacetate, 1:1)

Sources & evidence

ORD record
ord-a9d7e618868c4746abbca57a7502001a
Source dataset
uspto-grants-2010_12
Patent number
US07851629B2

Reaction notes

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