Cyclohexene → 4-(Trifluoromethyl)-4-piperidinol

HRID 1676262Notes

Reaction equation

HRID 1676262 reaction equation
[OH:1][C:2]1([C:18]([F:21])([F:20])[F:19])[CH2:7][CH2:6][N:5](C(OCC2C=CC=CC=2)=O)[CH2:4][CH2:3]1.C1CCCCC=1>CCO.[Pd]>[F:21][C:18]([F:19])([F:20])[C:2]1([OH:1])[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 57516616HCID 57516616, compound

Product 1

HCID 179513214-(Trifluoromethyl)-4-piperidinolYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of benzyl 4-hydroxy-4-(trifluoromethyl)piperidine-1-carboxylate (347 g, 1.15 mole) in EtOH (1.2 L) was added Pd—C (Degussa type, 10 wt. % Pd, 50% H2O, 26.0 g, 12.2 mmol) and cyclohexene (850 mL, 8.39 mol). The mixture was heated to a gentle reflux for 1 hour resulting in a slight exotherm and the vigorous evolution of gas. Upon cooling to ambient temperature, the mixture was filtered through Celite®, and the filtrate was concentrated. The resulting residue was dissolved in CH2Cl2 (500 mL), dried (Na2SO4), filtered, and concentrated to give an orange solid. The crude material was crystallized from MTBE to give 160 g (83%) of product as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 5.71 (br s, 1H), 2.74 (m, 4H), 2.42 (br s, 1H, overlaps DMSO), 1.53 (m, 4H).

Workup

  1. temperatureThe mixture was heated to
  2. temperaturea gentle reflux for 1 hour
  3. customresulting in a slight exotherm
  4. filtrationthe mixture was filtered through Celite®
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe resulting residue was dissolved in CH2Cl2 (500 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give an orange solid
  11. customThe crude material was crystallized from MTBE

Sources & evidence

ORD record
ord-27976153469e4fedaa6f3ebf15d6d6df
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

Loading…