3-Pyridinemethanamine → HCID 178419300, compound

HRID 580869Notes

Reaction equation

HRID 580869 reaction equation
[Br: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(Cl)Cl.CCCCCC.CCOCC.CCCCCC>C(OCCO)C>[Br: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

6

Reactant 4

HCID 310183-PyridinemethanamineHCID 12535780HCID 12535780, compoundHCID 21226440Methylenechloride HexaneHCID 21584099Diethylether hexane

Product 1

HCID 178419300HCID 178419300, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 0.4 g (1.3 mmol) of 8-bromo-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione (Sahni, S., et al., J. Indian Chem. Soc., 56:625 (1979)) in 10 mL of 2-ethoxyethanol was treated with 0.28 mL (2.1 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. Trituration with CH2Cl2 /hexane, then with Et2O/hexane left 0.3 g (61% yield) of the product as a yellow solid, mp 152-155° C. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =379.

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

Sources & evidence

ORD record
ord-73bc8ce7c28948359cfb12c9380d8420
Source dataset
uspto-grants-1999_07
Patent number
US05919780

Reaction notes

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