Dihexylamine → 4'-Bromo-di-n-hexylaminobutyrophenone

HRID 1441113Notes

Reaction equation

HRID 1441113 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][CH2:10][CH2:11]Cl)=[CH:4][CH:3]=1.[CH2:14]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH:9]([N:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH3:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8920DihexylamineHCID 783174'-Bromo-4-chlorobutyrophenone

Product 1

HCID 189812934'-Bromo-di-n-hexylaminobutyrophenone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 5.00 g of 4'-bromo-4-chlorobutyrophenone in 3 ml of toluene was added 11.1 ml of di-n-hexylamine and heated under reflux for 3 hours. After diluting with toluene, the reaction mixture was extracted with a 2N aqueous solution of hydrochloric acid. The extract was neutralized with a mass of sodium hydroxide and extracted with methylene chloride. Next, after drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, thereby giving 4.88 g of crude 4'-bromo-di-n-hexylaminobutyrophenone.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. extractionthe reaction mixture was extracted with a 2N aqueous solution of hydrochloric acid
  4. extractionextracted with methylene chloride
  5. dry with materialNext, after drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8098ddd8d4594518bdd0066add36c521
Source dataset
uspto-grants-1996_03
Patent number
US05502202

Reaction notes

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