3-Pyridinemethanamine → HCID 178477860, compound

HRID 580874Notes

Reaction equation

HRID 580874 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](=S)[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[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9]([NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 827106HCID 827106, compound

Product 1

HCID 178477860HCID 178477860, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 682 mg (2.5 mmol) of 8-chlorodibenzo[b,f]-1,4-thiazepin-11(10H)-thione (Polivka Z., et al., Coll. Czech. Chem. Comm., 48:1465 (1983)) in 15 mL of 2-ethoxyethanol was treated with 0.5 mL (5.0 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 (98/2) following by recrystallization from CHCl3 /hexane gave 600 mg (69.8% yield) of the product as a white solid, mp 152-153° C. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =352.

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 (98/2)
  8. customfollowing by recrystallization from CHCl3 /hexane

Sources & evidence

ORD record
ord-15bd494dee69444fba52081ecc3c033c
Source dataset
uspto-grants-1999_07
Patent number
US05919780

Reaction notes

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