Triethylamine → HCID 18328898, compound

HRID 1249728Notes

Reaction equation

HRID 1249728 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.Cl.O.[NH:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1.C(N(CC)CC)C>C(O)C>[Cl:9][C:4]1[N:3]=[C:2]([CH3:1])[N:7]=[C:6]([N:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)[CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2349974,6-Dichloro-2-methylpyrimidineHCID 2723901Piperonylamine

Product 1

HCID 18328898HCID 18328898, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-methyl-4,6-dichloropyrimidine (12.2 g), 4-piperidinone monohydrate monohydrochloride (10.9 g) and triethylamine (42 ml) in ethanol (300 ml) was heated to reflux. The resulting solution was stirred at reflux for 18 hours. The solution was evaporated to dryness. The solid residue was partitioned between ethyl acetate (1 l) and water (50 ml). The ethyl acetate layer was washed with water (3×50 ml), saturated brine (50 ml), dried (Na2SO4) and evaporated to dryness. The solid residue was recrystallised from ethyl acetate/isohexane to give a cream solid. This was further purified by column chromatography on alumina (ICN alumina N32-63), using dichloromethane as eluent, to give 1-(6-chloro-2-methylpyrimidin-4-yl)piperidin-4-one (14.0 g) as an off-white solid.

Workup

  1. temperaturewas heated to reflux
  2. temperatureat reflux for 18 hours
  3. customThe solution was evaporated to dryness
  4. customThe solid residue was partitioned between ethyl acetate (1 l) and water (50 ml)
  5. washThe ethyl acetate layer was washed with water (3×50 ml), saturated brine (50 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness
  8. customThe solid residue was recrystallised from ethyl acetate/isohexane
  9. customto give a cream solid
  10. customThis was further purified by column chromatography on alumina (ICN alumina N32-63)

Sources & evidence

ORD record
ord-cea27fcd2bcc4ce5b2713bcf616b87cc
Source dataset
uspto-grants-2002_01
Patent number
US06335341B1

Reaction notes

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