HCID 70873537, compound → HCID 70873738, compound

HRID 2172204Notes

Reaction equation

HRID 2172204 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=1)[CH2:14][CH2:13][CH2:12]2)C1C=CC=CC=1>C(O)C.[Pd]>[F:32][C:30]([F:31])([F:33])[O:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:21][CH2:20][CH2:19][N:15]2[C:16]3[C:11](=[CH:10][C:9]([OH:8])=[CH:18][CH:17]=3)[CH2:12][CH2:13][CH2:14]2)=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 70873537HCID 70873537, compound

Product 1

HCID 70873738HCID 70873738, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-Benzyloxy-1-[3-(4-trifluoromethoxy-phenoxy)propyl]-1,2,3,4-tetrahydro-quinoline (2.13 g) was dissolved in ethanol (10 ml). 10% palladium on carbon (0.2 g) was added thereto and stirred at room temperature under a hydrogen atmosphere for 4 hours. The mixture was filtered through Celite to remove the catalyst, and then the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) and concentrated under reduced pressure to afford the title compound (1.45 g).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5fa00c7524ca42099c7b165a8a25da2a
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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