Hydrochloric Acid → N-(4-piperidin-4-yl-butyl)-3-(pyridin-3-yl)-propionamide

HRID 1280769Notes

Reaction equation

HRID 1280769 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:28])[CH2:20][CH2:21][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH2:10][CH2:9]2)C=CC=CC=1.Cl.[H][H]>C(O)C.[Pd]>[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:28])[CH2:20][CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9846838N-[4-(1-diphenylmethylpiperidin-4-yl)-butyl]-3-(pyridin-3-yl)-propionamideHCID 178418361HCID 178418361, compound

Product 1

HCID 18425707N-(4-piperidin-4-yl-butyl)-3-(pyridin-3-yl)-propionamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

100 g (219.5 mmol) N-[4-(1-diphenylmethylpiperidin-4-yl)-butyl]-3-(pyridine-3-yl)-propionamide (substance 100) are dissolved in 500 ml ethanol and mixed with 8.0 g palladium (5%) on activated carbon (moistened with 40 ml water) and 25 ml conc. hydrochloric acid. The mixture is heated to ca. 45° C. and stirred under hydrogen atomosphere until consumption of the theoretical amount of hydrogen to be taken up (ca. five hours). After cooling, the catalyst is filtered and the solvent is removed under vacuum. The residue is taken up in 200 ml water and washed three times with a total of 200 ml CHCl3. The organic phases are discarded and the aqueous phase is made alkaline with 11 g sodium hydroxide and extracted three times, each with 100 ml CHCl3. After washing the organic phase with 30 ml water, the solvent is removed under vacuum. The oily residue is filtered over silica gel with CHCl3/CH3OH/NH4OH (80/20/2). Yield of the gradually hardening resin 53.0 g (83%).

Workup

  1. custom(ca. five hours)
  2. temperatureAfter cooling
  3. filtrationthe catalyst is filtered
  4. customthe solvent is removed under vacuum
  5. washwashed three times with a total of 200 ml CHCl3
  6. extractionextracted three times
  7. washAfter washing the organic phase with 30 ml water
  8. customthe solvent is removed under vacuum
  9. filtrationThe oily residue is filtered over silica gel with CHCl3/CH3OH/NH4OH (80/20/2)

Sources & evidence

ORD record
ord-63dfaa080d8147cda40bbdec04a594e1
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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