Acetic Acid → 2-Imino-4-methylpiperidine acetate

HRID 1459176Notes

Reaction equation

HRID 1459176 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[H][H].[C:11]([OH:14])(=[O:13])[CH3:12]>[Rh]>[C:11]([OH:14])(=[O:13])[CH3:12].[NH:1]=[C:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][CH2:4][NH:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 15332-Amino-4-methylpyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 1784758702-Imino-4-methylpiperidine acetate

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

2-Amino-4-methylpyridine (1.56 g; 15 mmoles) and 5% rhodium on carbon (0.51 g, wet, Degussa type G10) in glacial acetic acid (30 mL) were shaken on a Parr hydrogenation apparatus at 55 psi of hydrogen overnight. The catalyst was removed by filtration and the filtrate was diluted with water to 250 mL, and lyophilized to yield a light tan powder. The powder was recrystallized from warm ethanol/ether to give 0.3 g of white solid. mp 181°-182° C. A second crop of white solid was obtained (0.85 g; mp 180°-182° C.). MH+=113; 1H NMR (D2O): δ3.32-3.16 (m, 2H); 2.54-2.46 (m, 1H); 2.10-2.00 (m, 1H); 1.80-1.70 (m, 2H); 1.74 (s, 3H); 1.32-1.25 (m, 1H); 0.87 (d, J=6.6 Hz, 3H).

Workup

  1. customThe catalyst was removed by filtration
  2. additionthe filtrate was diluted with water to 250 mL
  3. customto yield a light tan powder
  4. customThe powder was recrystallized
  5. temperaturefrom warm ethanol/ether

Sources & evidence

ORD record
ord-b0b3cddaf6534bdb9b591f2ce353fab2
Source dataset
uspto-grants-1998_12
Patent number
US05854234

Reaction notes

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