Sodium Carbonate → HCID 15227522, compound

HRID 1742210Notes

Reaction equation

HRID 1742210 reaction equation
Cl.[CH2:2]([N:4]([CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[C:5](=[O:7])[CH3:6])[CH3:3].Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH2:2]([N:4]([CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]=2)[CH2:11][CH2:10]1)[C:5](=[O:7])[CH3:6])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 152943694-Chloro-2-(trifluoromethyl)pyrimidineHCID 19008884HCID 19008884, compound

Product 1

HCID 15227522HCID 15227522, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-ethyl-N-[(4-piperidinyl)methyl]acetamide hydrochloride (Example 4; 2.14 g, 10 Mole), 4-chloro-2-trifluoromethylpyrimidine (1.83 g, 10 mmole), and sodium carbonate (2.65 g, 25 mmole) in DMF (30 ml) was stirred for 18 hrs at room temperature. The mixture was concentrated in vacuo. The residue was dissolved in methylene chloride (50 ml), filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel using ethyl acetate as the eluent to give formula I product as a yellow oil (2.17 g, 67%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride (50 ml)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-e0f222d6b0af489e91b822e4e3256034
Source dataset
uspto-grants-1994_08
Patent number
US05338738

Reaction notes

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