Water → 681481-99-2

HRID 856031Notes

Reaction equation

HRID 856031 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:27])([F:26])[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][CH:18]([C:21](OCC)=[O:22])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.O.[OH-].[Na+]>C1COCC1>[F:26][C:8]([F:7])([F:27])[C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][OH:22])[CH2:17][CH2:16]2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23081565Ethyl 1-[4-(trifluoromethyl)phenyl]piperidine-4-carboxylate

Product 1

HCID 17768190681481-99-2Yield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (1.58 g, 41.64 mmol) was suspended in THF (30 ml), to which absolution of ethyl 1-(4-trifluoromethylphenyl)piperidine-4-carboxylate prepared in Reference Example 30 (3.18 g, 10.41 mmol) in THF (10 ml) was added dropwise therein while cooling in an ice-bath under a nitrogen atmosphere. The mixture was stirred for 30 minutes. Water and 10% sodium hydroxide aqueous solution were added to the reaction mixture, which was filtered through Celite. The filtrate was extracted with ethyl acetate twice. The extract was washed with water and brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to afford [1-(4-trifluoromethylphenyl)-piperidin-4-yl]methanol (2.64 g, yield 98%) as a pale yellow oil.

Workup

  1. additionwas added dropwise
  2. temperaturewhile cooling in an ice-bath under a nitrogen atmosphere
  3. filtrationwas filtered through Celite
  4. extractionThe filtrate was extracted with ethyl acetate twice
  5. washThe extract was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c020c910cad84345a281483b7e4b554f
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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