Butanal → HCID 28445475, compound

HRID 1441693Notes

Reaction equation

HRID 1441693 reaction equation
[NH2:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[CH:11](=O)[CH2:12][CH2:13][CH3:14].[BH4-].[Na+].C(OCC)(=O)C>CO>[CH2:11]([NH:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([C:2]#[N:1])=[CH:4][CH:5]=1)[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 261ButanalHCID 8857Ethyl AcetateHCID 826084-(Aminomethyl)benzonitrileHCID 4311764Sodium borohydride

Product 1

HCID 28445475HCID 28445475, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.0 g 4-Aminomethyl-benzonitrile and 3.75 ml Butyraldehyde were dissolved in 40 ml methanol. 3.0 g molecular sieves 4 Angström were added and the mixture was stirred at room temperature for two hours. Then 2.2 g sodium borohydride were added and the mixture was stirred for an additional hour at room temperature. 250 ml ethyl acetate were added, and the reaction was quenched by addition of 4 ml water. The reaction mixture was filtered through a pad of celite and MgSO4. The filtrate was evaporated in vacuo to provide 3.7 g crude 4-Butylaminomethyl-benzonitrile. This material was used without further purification.

Workup

  1. addition3.0 g molecular sieves 4 Angström were added
  2. stirringthe mixture was stirred for an additional hour at room temperature
  3. customthe reaction was quenched by addition of 4 ml water
  4. filtrationThe reaction mixture was filtered through a pad of celite and MgSO4
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c7f53e85df4545b09e21116f833e496a
Source dataset
uspto-grants-2010_02
Patent number
US07655679B2

Reaction notes

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