2,4-Dichlorobenzaldehyde → Cyclopropyl-(2,4-dichloro-benzyl)-amine

HRID 1072510Notes

Reaction equation

HRID 1072510 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH:11]1([NH2:14])[CH2:13][CH2:12]1.[BH4-].[Na+]>CO>[CH:11]1([NH:14][CH2:4][C:3]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=2[Cl:1])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 134042,4-DichlorobenzaldehydeHCID 69828CyclopropylamineHCID 4311764Sodium borohydride

Product 1

HCID 4720306Cyclopropyl-(2,4-dichloro-benzyl)-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.25 g (30 mmol) of 2,4-dichlorobenzaldehyde was introduced into 140 ml of methanol and, at room temperature, a solution of 1.71 g (30 mmol) of cyclopropylamine was added. The mixture as stirred at room temperature for 40 min and then 1.42 g (37.5 mmol) of NaBH4 was added in portions. After standing overnight, the solvent was removed and the residue was taken up in 2 N HCl. Two extractions with ethyl acetate were carried out. The aqueous phase was made alkaline with NaOH and again extracted twice with ethyl acetate. The organic phases were dried with MgSO4 and concentrated. The crude product obtained in this way, in the form of a slightly yellowish oil, was reacted further without further purification.

Workup

  1. waitAfter standing overnight
  2. customthe solvent was removed
  3. extractionTwo extractions with ethyl acetate
  4. extractionagain extracted twice with ethyl acetate
  5. dry with materialThe organic phases were dried with MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a8393593614e4b228a41f526143ec7c0
Source dataset
uspto-grants-2005_06
Patent number
US06911453B2

Reaction notes

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