Formic Acid → 4-(4-Methyl-1,4-diazepan-1-yl)benzaldehyde

HRID 1595370Notes

Reaction equation

HRID 1595370 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#N)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.C(O)=[O:18]>[Ni]>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:18])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 180011064-(4-Methyl-1,4-diazepan-1-yl)benzonitrile

Product 1

HCID 217040534-(4-Methyl-1,4-diazepan-1-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

4-(4-Methylhomopiperazin-1-yl)benzonitrile (15 g) was dissolved in formic acid (225 ml) and Raney nickel (15.5 g) was added. The mixture was refluxed under heating for 2.5 hr. After the reaction, the catalyst was filtered off and the mixture was concentrated under reduced pressure. The residue was neutralized with saturated aqueous potassium carbonate solution and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure to give the objective 4-(4-methylhomopiperazin-1-yl)benzaldehyde as an oil (16.1 g).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 2.5 hr
  3. customAfter the reaction
  4. filtrationthe catalyst was filtered off
  5. concentrationthe mixture was concentrated under reduced pressure
  6. extractionextracted with chloroform
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b32ef756b11f42d99bc6f26fc59a2a91
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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