Benzaldehyde → N-benzyl-4-fluoroaniline

HRID 487584Notes

Reaction equation

HRID 487584 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>O>[CH2:9]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 97314-FluoroanilineHCID 4311764Sodium borohydride

Product 1

HCID 913402N-benzyl-4-fluoroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-fluoroaniline (4.7 ml, 50 mmol), benzaldehyde (5.3 g, 50 mmol) and one crystal p-toluene-sulfonic acid is refluxed using a Dean-Stark® apparatus until no more water is collected and the mixture is concentrated in vacuo. The crude product is dissolved in 100 ml 96% ethanol and added sodium borohydride (4.0 g, 100 mmol) and stirred for 1 hour. Most of the ethanol is removed in vacuo and the residue is taken up in water and 15 g of potassium hydroxide in 50 ml water is added, causing the amine to crystallize. The product is recrystallized from methanol/water (in a ratio of 4 to 1) yielding the title compound as white crystals. Mp 38°-39° C.

Workup

  1. customis collected
  2. concentrationthe mixture is concentrated in vacuo
  3. dissolutionThe crude product is dissolved in 100 ml 96% ethanol
  4. customMost of the ethanol is removed in vacuo
  5. addition15 g of potassium hydroxide in 50 ml water is added
  6. customto crystallize
  7. customThe product is recrystallized from methanol/water (in a ratio of 4 to 1)

Sources & evidence

ORD record
ord-1065ebe3180c4c00bf796f054d786de3
Source dataset
uspto-grants-1994_03
Patent number
US05296493

Reaction notes

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