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

HRID 1965943Notes

Reaction equation

HRID 1965943 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. After 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 distilled 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. extractionAfter 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
  7. distillationthe amine is distilled in a water jet vacuum at a boiling point of 123° C.

Sources & evidence

ORD record
ord-a95b2330f7864603b6d06b26404b4ab6
Source dataset
uspto-grants-2013_04
Patent number
US08420630B2

Reaction notes

Loading…