1,4-Dioxane → HCID 53781673, compound

HRID 650625Notes

Reaction equation

HRID 650625 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH3:26])[C:8]([C:10]1[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:12][C:13](S(C)(=O)=O)=[N:14][CH:15]=1)=[O:9].O1[CH2:41][CH2:40]OCC1>>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH3:26])[C:8]([C:10]1[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:12][C:13]([N:7]2[CH2:41][CH2:40][CH2:4][CH2:5][CH2:6]2)=[N:14][CH:15]=1)=[O:9]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 54164811HCID 54164811, compound

Product 1

HCID 53781673HCID 53781673, compoundYield 191.4%

Procedure

To a solution of 0.5 g (0.96 mmol) 2-methylsulfonyl-4-phenyl-pyrimidine-5-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide in 10 ml dioxan 0.183 g (2.15 mmol) piperidin was added. The reaction mixture was stirred for 16 hrs. After evaporation of the solvent, the residue was distributed between 50 ml CH2Cl2 and 50 ml H2O. The aqueous layer was extracted with 50 ml CH2Cl2, the combined organic layers dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 20:1) to give 0.48 g (95%) 4-phenyl-2-piperidin-1-yl-pyrimidine-5-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a waxy pale yellow solid, MS (ISP): 523.2 (M+H+).

Workup

  1. customAfter evaporation of the solvent
  2. extractionThe aqueous layer was extracted with 50 ml CH2Cl2
  3. dry with materialthe combined organic layers dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-2b29f347a9204f7cbbaad530de5b8f69
Source dataset
uspto-grants-2001_08
Patent number
US06274588B1

Reaction notes

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