Pyrrolidine → 2-Methyl-6-[(pyrrolidin-1-yl)methyl]pyridine

HRID 1196520Notes

Reaction equation

HRID 1196520 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>C(O)C.[Pt]=O>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH2:8][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:7]=1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 707376-Methyl-2-pyridinecarboxaldehyde

Product 1

HCID 151232652-Methyl-6-[(pyrrolidin-1-yl)methyl]pyridineYield 65.9%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-methylpyridine-2-carboxaldehyde (1.2 g), pyrrolidine (0.78 g) and platinum oxide (0.15 g) in ethanol (50 ml) was hydrogenated at atmospheric pressure for 30 min. The catalyst was filtered off and the filtrate was evaporated. The residue (1.6 g) was purified by chromatography on alumina (60 g, Type UGI), eluting with ether-hexane (1:1) to give the title compound as a colourless mobile oil (1.15 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue (1.6 g) was purified by chromatography on alumina (60 g, Type UGI)
  4. washeluting with ether-hexane (1:1)

Sources & evidence

ORD record
ord-9cc6cae492794e15b3e4d9bf75c761de
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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