3-Pyridinemethanamine → HCID 178477815, compound

HRID 580870Notes

Reaction equation

HRID 580870 reaction equation
[Cl:1][C:2]1[C:17]([Cl:18])=[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.[NH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1>C(OCCO)C>[Cl:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]2[N:6]=[C:7]([NH:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=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 54123078HCID 54123078, compound

Product 1

HCID 178477815HCID 178477815, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 329 mg (1.1 mmol) of 7,8-dichloro-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione in 10 mL of 2-ethoxyethanol was treated with 0.3 mL (2.2 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. Chromatography on silica gel, eluting with CHCl3 /MeOH (97/3) followed by recrystallization from acetone/H2O gave 217 mg (52.8% yield) of the product as a yellow solid, mp 209-210° C. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =370.

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
  7. washChromatography on silica gel, eluting with CHCl3 /MeOH (97/3)
  8. customfollowed by recrystallization from acetone/H2O

Sources & evidence

ORD record
ord-f4d43b0ad0964a0aa1639fee789a7af4
Source dataset
uspto-grants-1999_07
Patent number
US05919780

Reaction notes

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