Acetic Acid → 5-(4-Chlorophenyl)-2-(1-methylpiperidin-4-yl)pyrimidine

HRID 1005892Notes

Reaction equation

HRID 1005892 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([C:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH:19]=3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.CO.C(O)(=O)C>C(OCC)(=O)C.[Pt](=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([CH:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 226466955-(4-Chlorophenyl)-2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine

Product 1

HCID 226466965-(4-Chlorophenyl)-2-(1-methylpiperidin-4-yl)pyrimidineYield 45%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Platinum(IV) oxide (30 mg) was added to a solution of 5-(4-chlorophenyl)-2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine (0.31 g) in a mixture of ethyl acetate (20 ml), methanol (3 ml) and acetic acid (1 ml) and the mixture was hydrogenated at atmospheric pressure for 18 h. The mixture was then filtered through celite, washing with 10% methanol/ethyl acetate, and evaporated under reduced pressure. The residue was treated with 2 M sodium hydroxide (15 ml) and extracted with diethyl ether (2×25 ml), and the organic extracts were washed with water (2×10 ml), saturated brine (20 ml), dried (Na2SO4) and evaporated under reduced pressure and the residue purified by silica gel column chromatography with 10% methanol/dichloromethane with 0.5% concentrated aqueous ammonia as eluent, to yield the title compound as a white solid (0.14 g, 45%).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washwashing with 10% methanol/ethyl acetate
  3. customevaporated under reduced pressure
  4. additionThe residue was treated with 2 M sodium hydroxide (15 ml)
  5. extractionextracted with diethyl ether (2×25 ml)
  6. washthe organic extracts were washed with water (2×10 ml), saturated brine (20 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customthe residue purified by silica gel column chromatography with 10% methanol/dichloromethane with 0.5% concentrated aqueous ammonia as eluent

Sources & evidence

ORD record
ord-0990ef0c7e214bd1bfe087e539f4b091
Source dataset
uspto-grants-2004_09
Patent number
US06787536B2

Reaction notes

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