Dibenzylamine → alpha-[[Bis(phenylmethyl)amino]methyl]-3-(methoxymethyl)-4-(phenylmethoxy)benzenemethanol

HRID 1165276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1165276
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([CH2:19][O:20][CH3:21])[CH:6]=1)=[O:4].[CH2:22]([NH:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:23]1([CH2:22][N:29]([CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:7]([CH2:19][O:20][CH3:21])[CH:6]=2)[OH:4])[CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

4

Edukt 2

HCID 7656DibenzylamineHCID 124989662-Bromo-1-[3-(methoxymethyl)-4-(phenylmethoxy)phenyl]ethanone

Produkt 1

HCID 19862717alpha-[[Bis(phenylmethyl)amino]methyl]-3-(methoxymethyl)-4-(phenylmethoxy)benzenemethanolAusbeute 85,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-bromo-1-[3-(methoxymethyl)-4-(phenylmethoxy)phenyl]ethanone (2.0 g), dibenzylamine (1.2 g) and DEA (0.8 g) in THF (30 ml) was allowed to stand at room temperature for 18 h, filtered and evaporated. The residual oil was dissolved in ethanol (20 ml) and treated portionwise with sodium borohydride (0.23 g), under nitrogen. The mixture was stirred at room temperature for 1 h, treated with methanol (20 ml), and evaporated. The residue was purified by FCC eluting with CX-ER (3:1) to give the title compound as an off-white solid (2.3 g), m.p. 52°-57°, t.l.c. (CX-ER 1:1) Rf 0.5

Aufarbeitung

  1. filtrationfiltered
  2. customevaporated
  3. dissolutionThe residual oil was dissolved in ethanol (20 ml)
  4. additiontreated portionwise with sodium borohydride (0.23 g), under nitrogen
  5. additiontreated with methanol (20 ml)
  6. customevaporated
  7. customThe residue was purified by FCC
  8. washeluting with CX-ER (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-d6936fe54de6497bac92ee75bf19e192
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04908386

Notizen zur Reaktion

Wird geladen…