Toluene → HCID 43163816, compound

HRID 1614893Notes

Reaction equation

HRID 1614893 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.[CH:12]1([NH2:15])[CH2:14][CH2:13]1.C1(C)C=CC=CC=1.[BH4-].[Na+]>ClCCl.O.CO>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH2:4][NH:15][CH:12]1[CH2:14][CH2:13]1

Participants

8

Reactant 4

HCID 1140TolueneHCID 69828CyclopropylamineHCID 3444802-Bromo-5-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 43163816HCID 43163816, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In a flask fitted with a Dean-Stark trap was introduced 2-bromo-5-methoxybenzaldehyde (5.68 g, 26.41 mmol), cyclopropylamine (3.02 g, 52.83 mmol) and toluene (70 ml). The reaction mixture was stirred at room temperature for 1 hour and then at reflux for 4 hours. The solution was then concentrated to give a yellow oil to which was added methanol (30 ml). The reaction mixture was cooled on icebath followed by portionwise addition of sodium borohydride (2.00 g, 52.83 mmol). After complete addition, the reaction mixture was stirred 2 hours at room temperature, and then water (70 ml) was added. The crude product was isolated by extraction with dichloromethane and the combined organic phases were dried over sodium sulfate, filtered, and finally evaporated under reduced pressure.

Workup

  1. customIn a flask fitted with a Dean-Stark trap
  2. temperatureat reflux for 4 hours
  3. concentrationThe solution was then concentrated
  4. customto give a yellow oil to which
  5. temperatureThe reaction mixture was cooled on icebath
  6. additionAfter complete addition
  7. stirringthe reaction mixture was stirred 2 hours at room temperature

Sources & evidence

ORD record
ord-bea219235cc346bca6eb4e273a38fed3
Source dataset
uspto-grants-2014_07
Patent number
US08765728B2

Reaction notes

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