N-Methylcyclohexylamine → 4-[[(N-cyclohexyl-N-methylamino)methylene]amino]-3-pyridinol

HRID 361329

Reaction equation

HRID 361329 reaction equation
[CH3:1][N:2]([CH:4]=[N:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[OH:12])[CH3:3].CN[CH:15]1[CH2:20][CH2:19]C[CH2:17][CH2:16]1>C1(C)C=CC=CC=1>[CH:3]1([N:2]([CH:4]=[N:5][C:6]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[OH:12])[CH3:1])[CH2:19][CH2:20][CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 7514N-MethylcyclohexylamineHCID 153809294-[[(Dimethylamino)methylene]amino]-3-pyridinol

Product 1

HCID 153809374-[[(N-cyclohexyl-N-methylamino)methylene]amino]-3-pyridinolYield 83.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-[[(dimethylamino)methylene]amino]-3-pyridinol (5.00 g), N-methylcyclohexylamine (5.20 g), and anhydrous toluene (50 mL) was heated at reflux under nitrogen for 17 hours. The solution was concentrated under reduced pressure and the crude product chromatographed on silica gel (10% methanol in dichloromethane) to afford 5.92 g of solid. Recrystallization from ethyl acetate/hexanes afforded 4.90 g of crystalline material, m.p. 127°-129° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 17 hours
  3. concentrationThe solution was concentrated under reduced pressure
  4. customthe crude product chromatographed on silica gel (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-73fb4cacfe7142d4ba70dc2957007909
Source dataset
uspto-grants-1999_02
Patent number
US05866565

Linked notes

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