Ethanol → HCID 70873672, compound

HRID 2172225Notes

Reaction equation

HRID 2172225 reaction equation
C(O)C.C([O:11][C:12]1[CH:37]=[CH:36][C:15]([CH:16]=[C:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH:30]4[CH2:35][CH2:34][CH2:33][CH2:32][O:31]4)=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[CH:14][CH:13]=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[O:31]1[CH2:32][CH2:33][CH2:34][CH2:35][CH:30]1[O:29][C:26]1[CH:27]=[CH:28][C:23]([N:20]2[CH2:21][CH2:22][CH:17]([CH2:16][C:15]3[CH:36]=[CH:37][C:12]([OH:11])=[CH:13][CH:14]=3)[CH2:18][CH2:19]2)=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 86709387HCID 86709387, compound

Product 1

HCID 70873672HCID 70873672, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Ethanol (20 ml) and ethyl acetate (10 ml) were added to 4-[4-(benzyloxy)benzylidene]-1-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]piperidine prepared in Reference Example 366. A palladium on carbon (0.378 g) was added to the mixture, and stirred at 50° C. for 4 hours under a hydrogen atmosphere. The insoluble matter was removed by filtration, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1→4:1) to afford the title compound as a colorless amorphous compound (1.10 g).

Workup

  1. customprepared in Reference Example 366
  2. customThe insoluble matter was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1→4:1)

Sources & evidence

ORD record
ord-fe318a0ae63841b4bc3b7fbc8505f5ee
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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