Water → 1-Benzyl-4-[4-chloro-3-(trifluoromethyl)phenyl]-4-piperidinol

HRID 2376645Notes

Reaction equation

HRID 2376645 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].C([O-])([O-])=O.[K+].[K+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>CN(C=O)C>[CH2:25]([N:11]1[CH2:10][CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:15]([F:18])([F:16])[F:17])[CH:4]=2)([OH:14])[CH2:13][CH2:12]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 891074-(4-Chloro-3-(trifluoromethyl)phenyl)piperidin-4-ol

Product 1

HCID 223451801-Benzyl-4-[4-chloro-3-(trifluoromethyl)phenyl]-4-piperidinol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 15 g of 4-[4-chloro-3-(trifluoromethyl)phenyl]-4-piperidinol, 8.3 g of K2CO3 and 7.18 ml of benzyl bromide in 80 ml of DMF is left with stirring at AT for 2 days. The reaction mixture is poured into water and extracted with AcOEt, an insoluble product is filtered off, the organic phase is washed with water and with saturated NaCl solution and dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, eluting with a DCM/MeOH (95/5; v/v) mixture. This gives 14.6 g of the expected product.

Workup

  1. waitis left
  2. extractionextracted with AcOEt
  3. filtrationan insoluble product is filtered off
  4. washthe organic phase is washed with water and with saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated under vacuum
  7. customThe residue is chromatographed on silica gel
  8. washeluting with a DCM/MeOH (95/5; v/v) mixture

Sources & evidence

ORD record
ord-e2e937b03622462b83cf0966e5ea0fe3
Source dataset
uspto-grants-2008_12
Patent number
US07468368B2

Reaction notes

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