3-Pyridinemethanamine → HCID 178420375, compound

HRID 580871Notes

Reaction equation

HRID 580871 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[C:15](=S)[NH:14][C:13]=2[CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1>C(OCCO)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[C:15]([NH:25][CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[N:14][C:13]=2[CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 54488434HCID 54488434, compound

Product 1

HCID 178420375HCID 178420375, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 0.6 g (1.8 mmol) of 8-benzyloxy-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione in 10 mL 2-ethoxyethanol was treated with 0.4 mL (3.6 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 with saturated NaHCO3 solution and saturated NaCl solution. Drying over MgSO4 and removal of the solvent under reduced pressure gave the crude product. After trituration with CHCl3 /hexane, recrystallization from MeOH gave 349 mg (47.8% yield) of the product as a yellow solid, mp 196-197° C. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =407.

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. customgave the crude product
  7. customAfter trituration with CHCl3 /hexane, recrystallization from MeOH

Sources & evidence

ORD record
ord-2866eef49a624ec79990019e1198b1cc
Source dataset
uspto-grants-1999_07
Patent number
US05919780

Reaction notes

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