Methanol → 4-(Pyridin-4-ylaminomethyl)piperidine hydrochloride

HRID 1592860Notes

Reaction equation

HRID 1592860 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[C:21]([Cl:22])=[C:20](Cl)[N:19]=[C:18](Cl)[C:17]=2Cl)[CH2:10][CH2:9]1)=O)(C)(C)C.C([O-])(=O)C.[Na+].CO.[H][H]>[Pd].C(O)C>[ClH:22].[N:19]1[CH:20]=[CH:21][C:16]([NH:15][CH2:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 517045Sodium AcetateHCID 22677919HCID 22677919, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 694264434-(Pyridin-4-ylaminomethyl)piperidine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-t-butoxycarbonyl-4-(2,3,5,6-tetrachloropyridin-4-ylaminomethyl)piperidine (18.5 g, 43.1 mmol), sodium acetate (21.2 g, 259 mmol) and 5% palladium on activated carbon (9.17 g, 4.31 mmol) in ethanol (340 mL)/methanol (170 mL) is stirred rapidly under 1 atmosphere of hydrogen for 20 hours. After the atmosphere of hydrogen is replaced with argon the mixture is filtered through a bed of Celite™ washing with methanol. The mixture is concentrated in vacuo and the residue is taken into chloroform and saturated sodium bicarbonate solution. The phases are separated and the aqueous phase is extracted into chloroform (×2). The combined organic extracts are dried (sodium sulfate), filtered and concentrated in vacuo. The residue is taken into methanol (1.20 L) and hydrogen chloride gas is passed through the solution maintaining <20° C. The mixture is kept at this temperature for 7 hours before it is concentrated in vacuo giving 4-(pyridin-4-ylaminomethyl)piperidine hydrochloride.

Workup

  1. filtrationis filtered through a bed of Celite™
  2. washwashing with methanol
  3. concentrationThe mixture is concentrated in vacuo
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted into chloroform (×2)
  6. dry with materialThe combined organic extracts are dried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. temperaturemaintaining <20° C
  10. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-bbcde3e0425a40408c9db10fcab044f2
Source dataset
uspto-grants-2007_11
Patent number
US07294627B2

Reaction notes

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