Pentylamine → 193557-31-2

HRID 1634540Notes

Reaction equation

HRID 1634540 reaction equation
[CH2:1]([NH2:6])[CH2:2][CH2:3][CH2:4][CH3:5].[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=O.S([O-])([O-])(=O)=O.[Mg+2]>>[CH2:1]([N:6]=[CH:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][N:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 3

HCID 8060PentylamineHCID 142732-PyridinecarboxaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 9812907193557-31-2

Procedure

n-Pentylamine (20.3 g, 0.23 mol) was added dropwise to pyridine-2-carboxaldehyde (25.0 g, 0.23 mol) with stirring in an ice bath. After complete addition of the amine, anhydrous magnesium sulfate (6 g) was added and the slurry stirred for 2 hours at 25° C. The solution was filtered, solvent removed, and the product purified by distillation under reduced pressure (0.5 mm Hg at 80° C.) to give a yellow oil. Yield: 29.6 g (73%). 1H NMR (CDCl3, 500 MHz): δ8.64 (m, 1H), 8.38 (s, 1H), 7.99 (m, 1H), 7.72 (m, 1H), 7.28 (m, 1H), 3.67 (t, 2H), 1.73 (sextet, 2H), 1.36 (overlapping quintets, 2H each), 0.90 (t, 3H), GCMS m/e 176.

Workup

  1. additionwas added
  2. stirringthe slurry stirred for 2 hours at 25° C
  3. filtrationThe solution was filtered
  4. customsolvent removed
  5. distillationthe product purified by distillation under reduced pressure (0.5 mm Hg at 80° C.)
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-8396e2df80094ccb961fddbec92cdae7
Source dataset
uspto-grants-2003_01
Patent number
US06506859B1

Reaction notes

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