HCID 23468748, compound → HCID 20329451, compound

HRID 2057933Notes

Reaction equation

HRID 2057933 reaction equation
[ClH:1].C([N:9]1[CH2:14][CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)([OH:15])[CH2:10]1)C1C=CC=CC=1.[H][H]>C(O)C.[OH-].[Pd+2].[OH-]>[ClH:1].[F:25][C:22]([F:23])([F:24])[C:18]1[CH:17]=[C:16]([C:11]2([OH:15])[CH2:12][CH2:13][CH2:14][NH:9][CH2:10]2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 23468748HCID 23468748, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20329451HCID 20329451, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of gaseous hydrogen chloride in ethyl acetate was added dropwise to a solution of 64 g of 1-benzyl-3-(3-trifluoromethyl-phenyl)-piperidine-3-ol in 100 ml of ethyl acetate until the pH was acidic and the mixture was vacuum filtered. The recovered product was washed with ethyl acetate and was dried under reduced pressure to obtain 62.5 g of 1-benzyl-3-(3-trifluoromethyl-phenyl)-piperidine-3-ol hydrochloride which sublimed towards 240° C. A suspension of 60 g of the said hydrochloride in 2.4 liters of ethanol was admixed with 12 g of activated carbon containing 10% by weight of palladium hydroxide and 4.2 liters of hydrogen was bubbled therethrough at 20° C. in 2 hours. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was crystallized from 100 ml of methanol and the mixture was vacuum filtered at 5° C. The recovered product was washed with iced methanol and dried at 35° C. to obtain 43.6 g of 3-(3-trifluoromethyl-phenyl)-piperidine-3-ol hydrochloride melting at 210° C.

Workup

  1. customsublimed towards 240° C
  2. customwas bubbled
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated to dryness under reduced pressure
  5. customThe residue was crystallized from 100 ml of methanol
  6. filtrationfiltered at 5° C
  7. washThe recovered product was washed with iced methanol
  8. customdried at 35° C.

Sources & evidence

ORD record
ord-3aea6c03c5b94e05a092d1e7eb135b96
Source dataset
uspto-grants-1980_07
Patent number
US04213989

Reaction notes

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