Potassium Carbonate → Pyridine-4-carboxaldehyde (3-Chloropropyl)imine

HRID 325100Notes

Reaction equation

HRID 325100 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH2:5][NH2:6].[N:7]1[CH:12]=[CH:11][C:10]([CH:13]=O)=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+]>O>[Cl:2][CH2:3][CH2:4][CH2:5][N:6]=[CH:13][C:10]1[CH:11]=[CH:12][N:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133894-PyridinecarboxaldehydeHCID 114690951-Propanamine, 3-chloro-, hydrochloride

Product 1

HCID 10655047Pyridine-4-carboxaldehyde (3-Chloropropyl)imine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3-chloropropylamine HCl (15.1 g, 0.120 moles (hereinafter mol)) and H2O (100 mL) was added pyridine-4-carboxaldehyde (9.55 mL, 0.100 mol), then K2CO3 (8.28 g, 0.060 mol) then CH2CL2 (100 mL) and the mixture was stirred for 40 min. The phases were separated and the aq phase was extracted with additional CH2Cl2 (2×50 mL), dried (Na2SO4) and concentrated to afford 17.1 g (94%) 1H NMR (CD3Cl): d 8.69 (d, J=4.5 Hz, 2H, 8.32 (s, 1H), 8.28 (s, 1H), 7.58 (d, J=4.5 Hz, 2H), 3.71 (m, 2H), 3.63 (t, J=6 Hz, 2H), 2.24 (t, J=6 Hz, 2H). The presence of 9% of the aldehyde was evident by 1H NMR.

Workup

  1. customThe phases were separated
  2. extractionthe aq phase was extracted with additional CH2Cl2 (2×50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto afford 17.1 g (94%) 1H NMR (CD3Cl): d 8.69 (

Sources & evidence

ORD record
ord-f5dc89926fb744dbae3dbf00f35ac64d
Source dataset
uspto-grants-2001_04
Patent number
US06222036B1

Reaction notes

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