2-(Morpholinomethyl)-pyridine → 4-((Piperidin-2-yl)methyl)morpholine

HRID 465050Notes

Reaction equation

HRID 465050 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H][H]>C(O)(=O)C.[Pt](=O)=O>[N:1]1([CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][NH:9]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2696942-(Morpholinomethyl)-pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 31633954-((Piperidin-2-yl)methyl)morpholineYield 52.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

First, 2-[(4-morpholinyl)methyl]pyridine (94.0 g, 0.53 mol) is dissolved in glacial acetic acid (600 ml) and hydrogenated in the presence of platinum(IV) oxide (10.0 g) as catalyst for 2 hours at a hydrogen pressure of 3 bar and a temperature of 50° C. After cooling, the catalyst is filtered off, the filtrate is freed from solvent and the residue is distilled in vacuo. The desired compound (51.0 g) is obtained in the form of a colorless liquid, boiling point 4 mm Hg 91°-92° C.

Workup

  1. customa temperature of 50° C
  2. temperatureAfter cooling
  3. filtrationthe catalyst is filtered off
  4. distillationthe residue is distilled in vacuo

Sources & evidence

ORD record
ord-6c56b257a38d47f38fb5eebc01b1ff4f
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Reaction notes

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