2-Pyridinecarboxaldehyde → 1-(pyridin-2-yl)-N-[(1R,2R)-2-{[(pyridin-2-yl)methylidene]amino}cyclohexyl]methanimine

HRID 857829Notes

Reaction equation

HRID 857829 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH2:8].[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=O>CO>[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=[N:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[N:8]=[CH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=1

Participants

4

Reactant 2

HCID 142732-PyridinecarboxaldehydeHCID 438061,2-Diaminocyclohexane, trans-

Product 1

HCID 100629331-(pyridin-2-yl)-N-[(1R,2R)-2-{[(pyridin-2-yl)methylidene]amino}cyclohexyl]methanimine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15.0 g (0.13 mol) of trans-1,2-diaminocyclohexane are dissolved in 80 ml of methanol and, at room temperature, 28.1 g (0.26 mol) of pyridine-2-aldehyde are added a little at a time. The solution is refluxed for one hour and then cooled to room temperature. The precipitated solid is filtered off and dried in an oil pump vacuum. The product is obtained in the form of a light-yellow powder in a yield of 23 g (79 mmol, 60%). 1H-NMR (400 MHz, CDCl3): δ=8.55 (m, 2H, Py), 8.31 (s, 2H, ═C—H), 7.88, 7.63, 7.21 (3×m, 6H, Py), 3.52 (m, 2H, NC—H), 1.90–1.49 (m, 8H, (CH2)4) ppm.

Workup

  1. temperatureThe solution is refluxed for one hour
  2. filtrationThe precipitated solid is filtered off
  3. customdried in an oil pump vacuum
  4. customThe product is obtained in the form of a light-yellow powder in a yield of 23 g (79 mmol, 60%)

Sources & evidence

ORD record
ord-9a344a5e80f2460db85d783760a81afd
Source dataset
uspto-grants-2006_12
Patent number
US07148174B2

Reaction notes

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