544696-02-8 → HCID 69431592, compound

HRID 1592855Notes

Reaction equation

HRID 1592855 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([Cl:23])[N:18]=2)[CH3:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[H][H]>[Pd].C(O)C.C([O-])(=O)C.[Na+]>[ClH:23].[N:20]1[CH:21]=[CH:22][C:17]([N:15]([CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH3:16])=[N:18][CH:19]=1

Participants

6

Reactant 2

HCID 71647831544696-02-8HCID 178418361HCID 178418361, compound2×

Product 1

HCID 69431592HCID 69431592, compoundYield 123.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 517045Sodium AcetateSolvent

Procedure

A suspension of 1-t-butoxycarbonyl-4-{[(2-chloropyrimidin-4-yl)(methyl)amino]methyl}piperidine (3.00 g, 8.80 mmol) and 5% palladium on activated carbon (1.87 g, 0.880 mmol) in ethanol (70 mL) and 1N sodium acetate solution (17.6 mL) is stirred rapidly under 1 atmosphere of hydrogen for 2 hours. After the atmosphere of hydrogen is replaced with argon the mixture is filtered through a bed of Celite™ and ethyl acetate, water and saturated sodium bicarbonate are added to the solution. The phases are separated and the aqueous phase is extracted into ethyl acetate (×3). The combined organic extracts are dried (sodium sulfate), filtered and concentrated in vacuo. The residue is taken into methanol (270 mL) and hydrogen chloride gas is passed through the solution maintaining <20° C. The mixture is kept at this temperature for 2 hours before it is concentrated in vacuo and freeze-dried from water providing 4-{[(pyrimidin-4-yl)(methyl)amino]methyl}piperidine hydrochloride (2.63 g, 100%).

Workup

  1. filtrationis filtered through a bed of Celite™ and ethyl acetate, water and saturated sodium bicarbonate
  2. additionare added to the solution
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted into ethyl acetate (×3)
  5. dry with materialThe combined organic extracts are dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. temperaturemaintaining <20° C
  9. concentrationis concentrated in vacuo
  10. dry with materialfreeze-dried from water

Sources & evidence

ORD record
ord-b90d2cd256c047e8a79f45ae33577bb9
Source dataset
uspto-grants-2007_11
Patent number
US07294627B2

Reaction notes

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