Sodium Hydroxide → HCID 53853565, compound

HRID 2419458Notes

Reaction equation

HRID 2419458 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[H][H].[OH-].[Na+]>[Pt]=O.C(O)(=O)C>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 22748793HCID 22748793, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53853565HCID 53853565, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 15.7 parts of 4-[α-(p-trifluoromethylphenyl)benzyl]pyridine in 250 parts of acetic acid is heated, with agitation, at 47° C. under approximately 4 atmospheres of hydrogen and in the presence of 2 parts of platinum oxide catalyst for 2 hours. The resultant mixture is filtered, and the filtrate is stripped of solvent by vacuum distillation. The residue is poured into 3 volumes of ice water, and the mixture thus obtained is made alkaline with sodium hydroxide. This mixture is then extracted with ether. The ether extract is dried over anhydrous potassium carbonate, filtered, and the ether removed to provide 4-[(4-trifluoromethylphenyl)phenylmethyl]piperidine as an oil.

Workup

  1. filtrationThe resultant mixture is filtered
  2. distillationthe filtrate is stripped of solvent by vacuum distillation
  3. additionThe residue is poured into 3 volumes of ice water
  4. customthe mixture thus obtained
  5. extractionThis mixture is then extracted with ether
  6. extractionThe ether extract
  7. dry with materialis dried over anhydrous potassium carbonate
  8. filtrationfiltered
  9. customthe ether removed

Sources & evidence

ORD record
ord-257187233b444ed883e2b296b3c73e55
Source dataset
uspto-grants-1978_08
Patent number
US04105849

Reaction notes

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