Acetic Acid → 4-[4-(Trifluoromethyl)phenyl]piperidin-4-ol

HRID 1578403Notes

Reaction equation

HRID 1578403 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([OH:24])([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)C.C(O)(=O)C.[OH-].[Na+]>[Pd].O>[OH:24][C:11]1([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 21559974HCID 21559974, compound

Product 1

HCID 152926054-[4-(Trifluoromethyl)phenyl]piperidin-4-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 10.0 g. (0.03 mol) of 1-benzyl-4-hydroxy-4-(α,α,α-trifluoro-p-tolyl)piperidine and 1.0 g. of 10% Pd/C in 100 ml. of ethanol containing 2.0 ml. of acetic acid is shaken under hydrogen. The mixture is filtered and the filtrate is evaporated to give a white solid which is dissolved in 50 ml. of water and rendered alkaline by addition of 1N NaOH solution. Filtration gives white crystals, m.p. 136°-138°C.

Workup

  1. additionA mixture of 10.0 g
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated
  4. customto give a white solid which
  5. dissolutionis dissolved in 50 ml
  6. filtrationFiltration
  7. customgives white crystals, m.p. 136°-138°C.

Sources & evidence

ORD record
ord-8716f96140e04d4098f0b6e55d7d782a
Source dataset
uspto-grants-1976_02
Patent number
US03936464

Reaction notes

Loading…