4-Benzylpiperidine → HCID 22353453, compound

HRID 1783333Notes

Reaction equation

HRID 1783333 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]=[C:10]([NH:20][C:21](=[O:26])[C:22]([O:24]C)=[O:23])[CH:9]=1)(=[O:3])[CH3:2].C(C1CCNCC1)C1C=CC=CC=1>CS(C)=O>[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]=[C:10]([NH:20][C:21](=[O:26])[C:22]([OH:24])=[O:23])[CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 317384-BenzylpiperidineHCID 20811457HCID 20811457, compound

Product 1

HCID 22353453HCID 22353453, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl [(6-{[2-(acetylamino)ethyl]amino}-2-phenylpyrimidin-4-yl)amino](oxo)acetate (50 mg) was dissolved in DMSO (420 μl) with stirring. To this were added 4-benzylpiperidine (74 μl) and activated powdered 4 angstrom molecular sieves and the mixture left to stir at room temperature for 5 hrs. After this time the reaction was filtered and first dichloromethane (1.6 ml) then PS-NCO (0.58 g) were added and the mixture left to stir for 1 hr. The resulting slurry was filtered, then partitioned between dichloromethane (20 ml) and water (20 ml), and the aqueous layer extracted with dichloromethane (2×20 ml). The combined organics were dried over magnesium sulfate, filtered and the solvent removed in vacuo. Further purification via column chromatography on silica gel eluting with a mixture of dichloromethane and methanol (94:6 v/v) furnished the title compound (33 mg).

Workup

  1. waitthe mixture left
  2. stirringto stir at room temperature for 5 hrs
  3. filtrationAfter this time the reaction was filtered
  4. additionfirst dichloromethane (1.6 ml) then PS-NCO (0.58 g) were added
  5. waitthe mixture left
  6. stirringto stir for 1 hr
  7. filtrationThe resulting slurry was filtered
  8. custompartitioned between dichloromethane (20 ml) and water (20 ml)
  9. extractionthe aqueous layer extracted with dichloromethane (2×20 ml)
  10. dry with materialThe combined organics were dried over magnesium sulfate
  11. filtrationfiltered
  12. customthe solvent removed in vacuo
  13. customFurther purification via column chromatography on silica gel eluting
  14. additionwith a mixture of dichloromethane and methanol (94:6 v/v)

Sources & evidence

ORD record
ord-3af1703d66fa4d3686b2ee715a5614b2
Source dataset
uspto-grants-2009_03
Patent number
US07501407B2

Reaction notes

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