Triethylamine → 1-Benzyl-4-[(1-[4-pyrimidinyl]-4-piperidyl)carbonyl]piperazine

HRID 2289521Notes

Reaction equation

HRID 2289521 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][N:4]=1.[CH2:9]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[O:23])[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>C(O)C>[CH2:9]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([CH:24]2[CH2:29][CH2:28][N:27]([C:3]3[CH:8]=[CH:7][N:6]=[CH:5][N:4]=3)[CH2:26][CH2:25]2)=[O:23])[CH2:18][CH2:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8839341-Benzyl-4-(piperidin-4-ylcarbonyl)piperazineHCID 219225564-Chloropyrimidine hydrochloride

Product 1

HCID 186980661-Benzyl-4-[(1-[4-pyrimidinyl]-4-piperidyl)carbonyl]piperazineYield 45.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloropyrimidine hydrochloride (3.5 g) was added to a stirred suspension of 1-benzyl-4-[4-piperidylcarbonyl]piperazine (6.6 g), triethylamine (12.8 ml) and ethanol (120 ml). The mixture was heated under reflux for four hours and evaporated in vacuo to yield a treacle like substance. The residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (Na2SO4) and evaporated. The residue was absorbed onto alumina and purified using dry flash chromatography eluting with increasingly polar mixtures of dichloromethane and methanol (1:0 to 98:2). The material obtained was triturated with diethylether to give 1-(benzyl)-4-[1 -(4-pyrimidinyl)-4-piperidylcarbonyl]piperazine (3.8 g, 45% yield), mp 107-108.5° C.;

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for four hours
  3. customevaporated in vacuo
  4. customto yield a treacle like substance
  5. customThe residue was partitioned between ethyl acetate and water
  6. washThe organic phase was washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe residue was absorbed onto alumina
  10. custompurified
  11. customusing dry flash chromatography
  12. washeluting
  13. temperaturewith increasingly polar mixtures of dichloromethane and methanol (1:0 to 98:2)
  14. customThe material obtained
  15. customwas triturated with diethylether

Sources & evidence

ORD record
ord-075f6a2d3c7e422d8d666685f1952bd3
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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