3-Bromoaniline → HCID 58200043, compound

HRID 1907262Notes

Reaction equation

HRID 1907262 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:15])[CH2:10][CH2:11][N:12]([CH3:14])C.[Br:16][C:17]1[CH:18]=C([CH:21]=[CH:22][CH:23]=1)N>C(O)C.O>[Br:16][C:17]1[CH:18]=[C:14]([NH:12][CH2:11][CH2:10][C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[Cl:2])=[O:15])[CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 241872721-(2-Chlorophenyl)-3-(dimethylamino)propan-1-one--hydrogen chloride (1/1)

Product 1

HCID 58200043HCID 58200043, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of 1-(2-chlorophenyl)-3-(dimethylamino)propan-1-one HCl salt (5.17 g, 20.85 mmol) and 3-bromoaniline (2.27 mL, 1 equiv) in 1:1 ethanol/water (21 mL, 1.0M) was heated at reflux overnight. LC-MS found the starting material was gone. The reaction mixture was cooled to rt. The ethanol was removed in vacuo. The residue was partitioned between EtOAc and water. The organic layer was washed with 1% aq HCl (2×30 mL), satd aq NaHCO3 solution (20 mL), brine (20 mL), and dried over Na2SO4. After filtration and concentration, the residue (6.08 g) was purified by chromatography on a 120-g silica cartridge to afford 3-(3-bromophenylamino)-1-(2-chlorophenyl)propan-1-one (2.75 g, 40% yield) as an orange oil. LC-MS (3 min) tR=2.03 min, m/z=340, 341(M+1); 1H NMR (CDCl3) δ 7.47(d, 1H), 7.44-7.38 (m, 2H), 7.33 (td, 1H), 7.00 (m, 1H), 6.84 (m, 1H), 6.77 (s, 1H), 6.56 (m, 1H).

Workup

  1. temperatureat reflux overnight
  2. customThe ethanol was removed in vacuo
  3. customThe residue was partitioned between EtOAc and water
  4. washThe organic layer was washed with 1% aq HCl (2×30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe residue (6.08 g) was purified by chromatography on a 120-g silica cartridge

Sources & evidence

ORD record
ord-984cd18d583d4ab2af4cc74a7a80f3c2
Source dataset
uspto-grants-2013_12
Patent number
US08598160B2

Reaction notes

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