3-Pyridinemethanamine → HCID 178477856, compound

HRID 580865Notes

Reaction equation

HRID 580865 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7](=S)[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[NH:10][C:4]=2[CH:3]=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:17]=[CH:16][C:5]2[N:6]=[C:7]([NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[NH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 24104717HCID 24104717, compound

Product 1

HCID 178477856HCID 178477856, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 0.41 g (1.57 mmol) of 7-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 2-ethoxyethanol was treated with 0.32 mL (3.14 mmol) of 3-(aminomethyl)pyridine and heated at reflux for 22 hours. The solvent was removed under reduced pressure and the residue mixed with EtOAc and filtered to give 0.31 g of product. The filtrate was concentrated and chromatographed on silica gel, eluting with EtOAc to give an additional 0.16 g of product. The material was combined and recrystallized from EtOAc/hexane to give 0.3 g (56.6% yield) of the product as a pale yellow solid, mp 218-220° C. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =335.

Workup

  1. temperatureheated
  2. temperatureat reflux for 22 hours
  3. customThe solvent was removed under reduced pressure
  4. additionthe residue mixed with EtOAc
  5. filtrationfiltered

Sources & evidence

ORD record
ord-98695265c70748dd9f7ce56d364f7c5d
Source dataset
uspto-grants-1999_07
Patent number
US05919780

Reaction notes

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