Ethyl 4-(4-oxopiperidin-1-yl)benzoate → Ethyl 4-(4-(2-(trifluoromethyl)benzylidene)piperidin-1-yl)benzoate

HRID 2196761Notes

Reaction equation

HRID 2196761 reaction equation
[Br-].[F:2][C:3]([F:31])([F:30])[C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.O=[C:38]1[CH2:43][CH2:42][N:41]([C:44]2[CH:54]=[CH:53][C:47]([C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:46][CH:45]=2)[CH2:40][CH2:39]1>C1COCC1>[F:31][C:3]([F:2])([F:30])[C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[CH:6]=[C:38]1[CH2:39][CH2:40][N:41]([C:44]2[CH:54]=[CH:53][C:47]([C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:46][CH:45]=2)[CH2:42][CH2:43]1

Participants

5

Reactant 3

HCID 12717442Ethyl 4-(4-oxopiperidin-1-yl)benzoateHCID 861853592-Trifluoromethylbenzyltriphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 67144747Ethyl 4-(4-(2-(trifluoromethyl)benzylidene)piperidin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 2-(trifluoromethyl)benzyl triphenylphosphonium bromide (prepared according to the procedure described in J. Chem. Soc. Perkin Trans. I 1995, 18, 2293-2308) (0.737 g) in THF (10 mL) was treated with n-butyllithium (724 μL, of a 1.6M solution in hexanes) at 0° C., treated with ethyl 4-(4-oxo-1-piperidinyl)benzoate (prepared according to the procedure described in Synthesis 1981, 606-608, 0.32 g), and gradually warmed to room temperature overnight. The reaction mixture was partitioned between ethyl acetate and saturated aqueous NH4Cl and the aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were dried (MgSO4), filtered, and concentrated. The resulting residue was purified by silica gel chromatography eluting with 10% ethyl acetate in hexanes to give the desired product.

Workup

  1. customprepared
  2. customprepared
  3. customdescribed in Synthesis 1981, 606-608, 0.32 g), and
  4. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous NH4Cl
  5. extractionthe aqueous layer was extracted with ethyl acetate (2×)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by silica gel chromatography
  10. washeluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f9f4942c4c234ebaa21a84c21b45acf7
Source dataset
uspto-grants-2012_12
Patent number
US08338466B2

Reaction notes

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