4-Bromobenzophenone → (4-Bromophenyl)(phenyl)methanamine

HRID 432185Notes

Reaction equation

HRID 432185 reaction equation
C([O-])=O.[NH4+:4].[Br:5][C:6]1[CH:19]=[CH:18][C:9]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)=[CH:8][CH:7]=1>>[Br:5][C:6]1[CH:19]=[CH:18][C:9]([CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH2:4])=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 70304-BromobenzophenoneHCID 2723923Ammonium formate

Product 1

HCID 350040(4-Bromophenyl)(phenyl)methanamineYield 72.5%

Conditions

Temperature
150 °C

Procedure

Ammonium formate (20.1 g, 0.318 mol) was placed in a 3-neck flask equipped with temperature controller, mechanical stirrer and a condenser and heated at 150° C. 4-bromobenzophenone (7.2 g, 0.0276 mol) was added at once, the temperature was raised to 165° C. and the mixture was stirred at reflux for twnety-four hours. The reaction mixture was cooled to ambient temperature, triturated in ethyl acetate (350 mL), treated with charcoal and filtered through a Celite pad. The filtrate was concentrated, suspended in concentrated hydrochloric acid (120 mL) and heated at reflux for 8 hours. The reaction mixture was cooled to ambient temperature and the precipitate was collected by filtration. It was triturated in water (120 mL), basified with saturated solution of sodium bicarbonate in water and extracted with ethyl acetate (2×250 mL). The combined organic extracts were dried with magnesium sulfate and concentrated under reduced pressure to yield (4-bromophenyl)(phenyl) methanamine (5.25 g, 0.02 mol) as a white solid.

Workup

  1. customequipped with temperature controller, mechanical stirrer and a condenser
  2. temperaturewas raised to 165° C.
  3. temperatureat reflux for twnety-four hours
  4. temperatureThe reaction mixture was cooled to ambient temperature
  5. customtriturated in ethyl acetate (350 mL)
  6. additiontreated with charcoal
  7. filtrationfiltered through a Celite pad
  8. concentrationThe filtrate was concentrated
  9. temperatureheated
  10. temperatureat reflux for 8 hours
  11. temperatureThe reaction mixture was cooled to ambient temperature
  12. filtrationthe precipitate was collected by filtration
  13. customIt was triturated in water (120 mL)
  14. extractionextracted with ethyl acetate (2×250 mL)
  15. dry with materialThe combined organic extracts were dried with magnesium sulfate
  16. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-99b86faa767942cf8a018f57b7511045
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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