3-Pyridinemethanamine → HCID 178479881, compound

HRID 580873Notes

Reaction equation

HRID 580873 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[C:8](=S)[NH:7][C:6]=2[CH:18]=1.[NH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1>C(OCCO)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[C:8]([NH:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[N:7][C:6]=2[CH:18]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 54101866HCID 54101866, compound

Product 1

HCID 178479881HCID 178479881, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 329 mg (1.2 mmol) of 8-chloro-5-methyl-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione (Hunziker F., et al., Helv. Chim. Acta, 50:1588 (1967)) in 10 mL of 2-ethoxyethanol was treated with 0.3 mL (2.4 mmol) of 3-(aminomethyl)pyridine and heated at reflux overnight. The solvent was removed under reduced pressure and the residue taken up in EtOAc and washed three times with H2O, then saturated NaHCO3 solution and saturated NaCl solution. Drying over MgSO4 and removal of the solvent under reduced pressure left the crude product as an oil. Chromatography on silica gel, eluting with CHCl3 /MeOH (98/2) gave 160 mg (38.4% yield) of the product as a golden solid foam. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =349.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. washwashed three times with H2O
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  6. waitleft the crude product as an oil
  7. washChromatography on silica gel, eluting with CHCl3 /MeOH (98/2)

Sources & evidence

ORD record
ord-b00291a578f644a78f4fd609f9e1a9ac
Source dataset
uspto-grants-1999_07
Patent number
US05919780

Reaction notes

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