2-Methyl-6-[(pyrrolidin-1-yl)methyl]pyridine → HCID 86745841, compound

HRID 1196521Notes

Reaction equation

HRID 1196521 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1>C(O)(=O)C.[Pt]=O>[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[NH:3]1

Participants

4

Reactant 1

HCID 151232652-Methyl-6-[(pyrrolidin-1-yl)methyl]pyridine

Product 1

HCID 86745841HCID 86745841, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of the product of stage (i) (1.0 g) and platinum oxide (0.25 g) in acetic acid was hydrogenated at 80 p.s.i. for 18 h. The catalyst was filtered off, and the filtrate was evaporated in vacuo. The residue was dissolved in dichloromethane and washed with 2N sodium hydroxide and water. The organic extracts were dried (MgSO4) and evaporated and the residue (1.0 g) was purified by chromatography on alumina (60 g, UGI) eluting with ether hexane (1:1) to give the title compound (0.65 g) as an oil. T.l.c. Alumina-dichloromethane-ethanol (20:1), Rf 0.8.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with 2N sodium hydroxide and water
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. customevaporated
  7. customthe residue (1.0 g) was purified by chromatography on alumina (60 g, UGI)
  8. washeluting with ether hexane (1:1)

Sources & evidence

ORD record
ord-13f1edecf4924ab0ae0cd9f1a469f950
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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