Benzaldehyde → 1-Benzyl-hexahydro-4H-azepin-4-one

HRID 1253736Notes

Reaction equation

HRID 1253736 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH2:3][CH2:2]1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:9]([N:1]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH2:3][CH2:2]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 1501891Azepan-4-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 15143501-Benzyl-hexahydro-4H-azepin-4-oneYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of azepan-4-one (8.0 g, 53.47 mmol, 1.0 eq.) in methylene chloride (100 ml) was added TEA followed by benzaldehyde and reaction mixture was stirred at RT for 30 min. Na(OAc)3BH was added portionwise to the reaction mixture and it was then stirred at RT for another 4 h. The reaction mixture was quenched with NaOH (2 M, 80 ml) and extracted with methylene chloride (3×100 ml). The organic layer was dried over Na2SO4 and solvent was evaporated under reduced pressure to afford the crude product which was purified by column chromatography (silica gel, 20% EtOAc/hexanes) to yield the desired product as an oil. Yield: 78% (8.5 g, 41.87 mmol).

Workup

  1. additionwas added TEA
  2. stirringwas then stirred at RT for another 4 h
  3. customThe reaction mixture was quenched with NaOH (2 M, 80 ml)
  4. extractionextracted with methylene chloride (3×100 ml)
  5. dry with materialThe organic layer was dried over Na2SO4 and solvent
  6. customwas evaporated under reduced pressure
  7. customto afford the crude product which
  8. customwas purified by column chromatography (silica gel, 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-51a91f3063da46ff8a27b11bfc855e5c
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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