N-(3-Pyridylmethyl)Pyrrolidine → 3-(Pyrrolidin-1-ylmethyl)piperidine

HRID 2233142Notes

Reaction equation

HRID 2233142 reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)(=O)C.O=[Pt]=O>[N:1]1([CH2:6][CH:7]2[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 67786N-(3-Pyridylmethyl)Pyrrolidine

Product 1

HCID 43418943-(Pyrrolidin-1-ylmethyl)piperidine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

The educt 3-(1-pyrrolidinylmethyl)-pyridine (24.6 g) is taken up in 250 ml glacial acetic acid and hydrogenated with 2 g of PtO2 under 3 bar H2 at ambient temperature. The solution filtered off is evaporated down, combined with ice and made alkaline with solid KOH while cooling. Afer extracting three times with 250 ml of diethylether the crude product is dried with MgSO4. After the MgSO4 has been filtered off the solvent is eliminated and the amine is distillled in a water jet vacuum at a boiling point of 123° C.

Workup

  1. filtrationThe solution filtered off
  2. customis evaporated down
  3. temperaturewhile cooling
  4. extractionAfer extracting three times with 250 ml of diethylether the crude product
  5. dry with materialis dried with MgSO4
  6. filtrationAfter the MgSO4 has been filtered off the solvent

Sources & evidence

ORD record
ord-11e6ccb43d0f4476898481a52cec11e6
Source dataset
uspto-grants-2010_05
Patent number
US07709480B2

Reaction notes

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