Ethanol → HCID 19363748, compound

HRID 866070Notes

Reaction equation

HRID 866070 reaction equation
Cl.C1(C[N:9]2[CH2:14][CH2:13][CH:12]([C:15]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[OH:16])[CH2:11][CH2:10]2)C=CC=CC=1.C(O)C.[H][H]>CO.[Pd]>[F:36][C:33]([F:34])([F:35])[C:30]1[CH:29]=[CH:28][C:27]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=2)([OH:16])[CH:12]2[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]2)=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 19363750HCID 19363750, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19363748HCID 19363748, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 10.0 grams (0.019 mole) of N-phenylmethyl-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine hydrochloride (prepared as in Steps A and B of Example 12) and 3.0 grams of 5% palladium (catalyst) on charcoal in about 200 mL of 1:1 methanol:ethanol was shaken in a Parr hydrogenator for five to six hours at about 85° C., until the theoretical amount of hydrogen gas was taken up. The mixture was cooled to ambient temperature where it stood for about 18 hours. The mixture was filtered and concentrated under reduced pressure to a residue, which was stirred with ethyl acetate and an aqueous solution saturated with sodium bicarbonate until the residue dissolved. The organic layer was separated and passed through phase-separation paper to remove aqueous material. The organic layer was concentrated under reduced pressure, yielding about 7.0 grams of 4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure to a residue, which
  3. dissolutionan aqueous solution saturated with sodium bicarbonate until the residue dissolved
  4. customThe organic layer was separated
  5. custompassed through phase-separation paper
  6. customto remove aqueous material
  7. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1e9b397738ea470c927cb547cb0e03cc
Source dataset
uspto-grants-1996_10
Patent number
US05569664

Reaction notes

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