Water → (4-Methoxy-phenyl)-[2-(3-methoxy-phenyl)-ethyl]-amine

HRID 853792Notes

Reaction equation

HRID 853792 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10](Cl)=O)[CH:6]=[CH:7][CH:8]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.O>C(OCC)(=O)C>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][CH2:10][CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7732P-AnisidineHCID 27332463-Methoxyphenylacetyl chloride

Product 1

HCID 10729848(4-Methoxy-phenyl)-[2-(3-methoxy-phenyl)-ethyl]-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of (3-methoxy-phenyl)-acetyl chloride (5.0 g) in ethyl acetate (85 mL) was added to a solution of 4methoxy-phenylamine (3.33 g) in ethyl acetate (50 mL). After 18 h the reaction was poured into water (150 mL). The organic extract was dried over sodium sulfate, filtered through celite and concentrated. The resulting residue was dissolved in tetrahydrofurane (100 mL) then lithium aluminum hydride (5.2 g) was added in small portions over 30 minutes. After 18 h the reaction was slowly poured onto 200 mL of ice. The mixture was filtered through a pad of celite and the collected filtrate was extracted with ethyl acetate (300 mL). The organic extract was dried over sodium sulfate, filtered through celite and concentrated to give the title compound. MS: 258.3 (MH+); HPLC tR: 1.98 min.

Workup

  1. extractionThe organic extract
  2. dry with materialwas dried over sodium sulfate
  3. filtrationfiltered through celite and
  4. concentrationconcentrated
  5. dissolutionThe resulting residue was dissolved in tetrahydrofurane (100 mL)
  6. additionlithium aluminum hydride (5.2 g) was added in small portions over 30 minutes
  7. additionAfter 18 h the reaction was slowly poured onto 200 mL of ice
  8. filtrationThe mixture was filtered through a pad of celite
  9. extractionthe collected filtrate was extracted with ethyl acetate (300 mL)
  10. extractionThe organic extract
  11. dry with materialwas dried over sodium sulfate
  12. filtrationfiltered through celite and
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-1db3272e79de40af940efe80d3d4e257
Source dataset
uspto-grants-2007_08
Patent number
US07256201B2

Reaction notes

Loading…