3-Pyridinecarboxaldehyde → 1-(3-Pyridyl)methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

HRID 347641Notes

Reaction equation

HRID 347641 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][CH2:4][CH2:3][CH2:2]1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=O)[CH:13]=1.[BH4-].[Na+]>C(O)(=O)C.CO>[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:1]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[NH:5][CH2:4][CH2:3][CH2:2]2)[CH:13]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 5771922,3,4,5-tetrahydro-1H-1,5-benzodiazepineHCID 4311764Sodium borohydride

Product 1

HCID 107763951-(3-Pyridyl)methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

To solution of 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine from Example 15A (0.50 g, 3.38 mmol) in 1% acetic acid/methanol (25 ml), at room temperature, was added pyridine-3-carboxaldehyde (0.35 ml, 03.72 mmol). The mixture was stirred at reflux for 18 h and then allowed to cool to room temperature. Sodium borohydride (0.050 g, 0.80 mmol) was added. The mixture was stirred for 2 h and then evaporated in vacuo. The residue was partitioned between EtOAc and saturated sodium bicarbonate solution. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacua. The residue was purified by flash chromatography on silica (eluant EtOAc) to give a white solid; yield 0.386 g (40%).

Workup

  1. temperatureat reflux for 18 h
  2. stirringThe mixture was stirred for 2 h
  3. customevaporated in vacuo
  4. customThe residue was partitioned between EtOAc and saturated sodium bicarbonate solution
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacua
  8. customThe residue was purified by flash chromatography on silica (eluant EtOAc)
  9. customto give a white solid

Sources & evidence

ORD record
ord-13ea9c02dc5f422abb7ab4c6cfbdf6ea
Source dataset
uspto-grants-2007_02
Patent number
US07176195B2

Reaction notes

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