Triethylamine → N1-(4-bromo-2-methoxyphenyl)-3-phenylpropanamide

HRID 432310

Reaction equation

HRID 432310 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:27])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18](=[O:27])[CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 4592574-Bromo-2-methoxyaniline

Product 1

HCID 22346842N1-(4-bromo-2-methoxyphenyl)-3-phenylpropanamideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-2-methoxyaniline (8.096 g, 40.04 mmol) in dichloromethane (100 mL) was treated with triethylamine (6.06 g, 60.06 mmol), then hydrocinnamoyl chloride (7.08 g, 42.04 mmol). The reaction mixture was stirred for 48 h under a nitrogen atmosphere. The solvent was removed under reduced pressure, and ethyl acetate was added. The precipitate was filtered, and the filtrate was evaporated to a solid under reduced pressure. The solid was dissolved in ethyl acetate, and washed with 5 N hydrochloric acid solution, 5 N sodium hydroxide solution, water and brine. The crude material (two spots by thin layer chromatography) was triturated with methanol. The un-dissolved solid was filtered to give 6 g (50%) of N1-(4-bromo-2-methoxyphenyl)-3-phenylpropanamide. 1H NMR (DMSO-d6, 400 MHz) δ 9.17 (s, 1H), 7.92-7.90 (m, 1H), 7.30-7.24 (m, 4H), 7.20-7.18 (m, 2H), 7.09-7.07 (m, 1H), 3.83 (s, 3H), 2.90-2.86 (m, 2H), 2.72-2.69 (m, 2H); HPLC Waters 2690 Alliance HPLC (Symmetry Shield RP18 3.5 μm, 2.1×50 mm; 5%-95% acetonitrile-0.1 M ammonium acetate over 15 min, 0.5 mL/min) Rt 7.491 min (97%).

Workup

  1. customThe solvent was removed under reduced pressure, and ethyl acetate
  2. additionwas added
  3. filtrationThe precipitate was filtered
  4. customthe filtrate was evaporated to a solid under reduced pressure
  5. dissolutionThe solid was dissolved in ethyl acetate
  6. washwashed with 5 N hydrochloric acid solution, 5 N sodium hydroxide solution, water and brine
  7. customThe crude material (two spots by thin layer chromatography) was triturated with methanol
  8. filtrationThe un-dissolved solid was filtered

Sources & evidence

ORD record
ord-9c35179e90b8407ca1ad7b0534e86143
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Linked notes

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