Sodium Acetate → HCID 69427274, compound

HRID 1592864Notes

Reaction equation

HRID 1592864 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([Cl:22])[N:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C([O-])(=O)C.[Na+].[H][H]>[Pd].C(O)C.O>[ClH:22].[N:19]1[CH:20]=[CH:21][C:16]([NH:15][CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[N:17][CH:18]=1

Participants

7

Reactant 3

HCID 517045Sodium AcetateHCID 58702213HCID 58702213, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 69427274HCID 69427274, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 1-t-butoxycarbonyl-4-[(2-chloropyrimidin-4-ylamino)methyl]piperidine (8.40 g, 25.7 mmol), sodium acetate (4.22 g, 51.4 mmol) and 5% palladium on activated carbon (5.47 g, 2.57 mmol) in ethanol (205 mL) and water (51 mL) is stirred rapidly under 1 atmosphere of hydrogen for 24 hours. After the atmosphere of hydrogen is replaced with argon the mixture is filtered through a bed of Celite™ and the mixture is concentrated in vacuo. Chloroform, water and saturated sodium bicarbonate are added, the phases are separated and the aqueous phase is extracted into chloroform (×3). The combined organic extracts are dried (sodium sulfate), filtered and concentrated in vacuo. The residue is taken into methanol (750 mL) and hydrogen chloride gas is passed through the solution maintaining the temperature at less than 20° C. The mixture is kept at this temperature for 24 hours before it is concentrated in vacuo and freeze-dried from water, providing 4-[(pyrimidin-4-ylamino)methyl]piperidine hydrochloride (5.82 g, 99%).

Workup

  1. filtrationis filtered through a bed of Celite™
  2. concentrationthe mixture is concentrated in vacuo
  3. additionChloroform, water and saturated sodium bicarbonate are added
  4. customthe phases are separated
  5. extractionthe aqueous phase is extracted into chloroform (×3)
  6. dry with materialThe combined organic extracts are dried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. temperaturemaintaining the temperature at less than 20° C
  10. concentrationis concentrated in vacuo
  11. dry with materialfreeze-dried from water

Sources & evidence

ORD record
ord-bbf8bd2e6f2e4877b34edd4a4ca38bb5
Source dataset
uspto-grants-2007_11
Patent number
US07294627B2

Reaction notes

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