2-(3,4-Dichlorophenoxy)-5-Fluoro-N-Methyl-Benzamide → 1-(2-(3,4-dichlorophenoxy)-5-fluorophenyl)-N-methylmethanamine

HRID 1839431

Reaktionsgleichung

Reaktionsgleichung von HRID 1839431
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:7]=1[C:8]([NH:10][CH3:11])=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:7]=1[CH2:8][NH:10][CH3:11]

Komponenten

3

Edukt 1

HCID 220192802-(3,4-Dichlorophenoxy)-5-Fluoro-N-Methyl-Benzamide

Produkt 1

HCID 98611241-(2-(3,4-dichlorophenoxy)-5-fluorophenyl)-N-methylmethanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Under N2, a mixture of 0.313 g (1.0 mmol) of 2-(3,4-dichlorophenoxy)-5-fluoro-N-methyl-benzamide in 5.0 mL of anhydrous tetrahydrofuran (THF) was treated via syringe with 4.0 mL (4.0 mmol) of 1.0 M BH3 in THF (Aldrich Chem. Co.). and the mixture was heated to reflux for a total of 48 hr. The reaction was quenched by the addition of 25 mL of 6N HCl and heating to reflux until the free amine could be detected by tlc (CHCl3:CH3OH:TEA, (95:5:1)). The cooled mixture was then diluted with water, basified with K2CO3and extracted with EtOAc. The combined organic layers were washed with water and saturated NaCl, then dried with MgSO4, filtered and concentrated in vacuo to the free base as a light brown oil, 0.164 g, 54%). This compound was converted to the hydrochloride salt as described previously, m.p. 200-202°.

Aufarbeitung

  1. additionwas treated via syringe with 4.0 mL (4.0 mmol) of 1.0 M
  2. temperatureand the mixture was heated
  3. temperatureto reflux for a total of 48 hr
  4. customThe reaction was quenched by the addition of 25 mL of 6N HCl
  5. temperatureheating
  6. temperatureto reflux until the free amine
  7. additionThe cooled mixture was then diluted with water
  8. extractionextracted with EtOAc
  9. washThe combined organic layers were washed with water and saturated NaCl
  10. dry with materialdried with MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo to the free base as a light brown oil, 0.164 g, 54%)

Quellen und Nachweise

ORD-Eintrag
ord-7c2015f983ea46f0a9ad3b89d36a2694
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06677378B2

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