Butanal → 4-(2-Butylamino-ethyl)-benzonitrile

HRID 1441687Notes

Reaction equation

HRID 1441687 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.[CH:12](=O)[CH2:13][CH2:14][CH3:15].[BH4-].[Na+].C(OCC)(=O)C>CO>[CH2:12]([NH:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 261ButanalHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 219125254-(2-Aminoethyl)benzonitrile

Product 1

HCID 591645764-(2-Butylamino-ethyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

700 mg 4-(2-Amino-ethyl)-benzonitrile and 63 μl Butyraldehyde were dissolved in 20 ml methanol. 1.0 g molecular sieves 4 Angström were added the mixture was stirred at room temperature for two hours. Then 270 mg sodium borohydride were added and the mixture was stirred for an additional hour at room temperature. 100 ml ethyl acetate were added, and the reaction was quenched by addition of 1 ml water. The reaction mixture was filtered through a pad of celite and MgSO4. The filtrate was evaporated in vacuo to provide 750 mg crude 4-(2-Butylamino-ethyl)-benzonitrile. This material was used without further purification.

Workup

  1. addition1.0 g molecular sieves 4 Angström were added the mixture
  2. stirringthe mixture was stirred for an additional hour at room temperature
  3. customthe reaction was quenched by addition of 1 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-96df91b9c81e4bd188f03779ff4c065c
Source dataset
uspto-grants-2010_02
Patent number
US07655679B2

Reaction notes

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