Sodium Methoxide → 1-Boc-4-[(pyrid-4-ylamino)methyl]piperidine

HRID 1837494Notes

Reaction equation

HRID 1837494 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[C:21](Cl)=[C:20](Cl)[N:19]=[C:18](Cl)[C:17]=2Cl)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[O-].[Na+]>CO.C1COCC1.[Pd]>[C:1]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][NH:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

6

Reactant 2

HCID 10942334Sodium MethoxideHCID 22677919HCID 22677919, compound

Product 1

HCID 226779521-Boc-4-[(pyrid-4-ylamino)methyl]piperidineYield 59%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-Boc-4-[(2,3,5,6-tetrachloropyrid-4-ylamino)methyl]piperidine (2.5 g, 5.83 mmol) in a mixture of methanol (23 mL) and THF (23 mL) was added sodium methoxide (1.89 g, 35 mmol) and 5% palladium on carbon (1.24 g). The mixture was hydrogenated for 30 h and the cataylst was filtered off and the solution concentrated in vacuo. The residue was taken up in ethyl acetate and washed with water and satd sodium bicarbonate. The aqueous washes were back extracted with ethyl acetate, and the combined organics dried (MgSO4) and concentrated in vacuo to give the product (1.0 g, 59%).

Workup

  1. filtrationthe cataylst was filtered off
  2. concentrationthe solution concentrated in vacuo
  3. washwashed with water
  4. extractionThe aqueous washes were back extracted with ethyl acetate
  5. dry with materialthe combined organics dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5af1fc7d32554ce3bb931c96f7a64dc0
Source dataset
uspto-grants-2004_08
Patent number
US06784182B2

Reaction notes

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