3-Pyridinemethanamine → HCID 178477858, compound

HRID 580860Notes

Reaction equation

HRID 580860 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8](=S)[NH:7][C:6]=2[CH:17]=1.[NH2:18][CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1>C(OCCO)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:7][C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 125357788-Chloro-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione

Product 1

HCID 178477858HCID 178477858, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 0.39 g (1.5 mmol) of 8-chloro-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 (2.99 mmol) of 3-(aminomethyl)pyridine and heated at reflux for 30 hours. The solvent was removed under reduced pressure and the residue mixed with EtOAc and filtered to give 200 mg of the product. The filtrate was chromatographed on silica gel, eluting with EtOAc to give an additional 200 mg of product. Total yield 400 mg (80% yield) of the product as a yellow solid, mp 230-234° C. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =335.

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 hours
  3. customThe solvent was removed under reduced pressure
  4. additionthe residue mixed with EtOAc
  5. filtrationfiltered

Sources & evidence

ORD record
ord-95aa7f681c6f403f9cc598d1adf29ce7
Source dataset
uspto-grants-1999_07
Patent number
US05919780

Reaction notes

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