1-(3,5-Bis(phenylmethoxy)phenyl)-2-bromoethan-1-one → 3,5-Bis(phenylmethoxy)-alpha-[[(phenylmethyl)[6-[[6-(2-pyridinyl)hexyl]-oxy]hexyl]amino]methyl]benzenemethanol

HRID 1088712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088712
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([C:23](=[O:26])[CH2:24]Br)[CH:12]=[C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][NH:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C=O)C>[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:23]([CH2:24][N:46]([CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][O:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=3)[OH:26])[CH:12]=[C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 1200971-(3,5-Bis(phenylmethoxy)phenyl)-2-bromoethan-1-oneHCID 22161746N-[6-[[6-(2-Pyridinyl)hexyl]oxy]hexyl]benzenemethanamine

Produkt 1

HCID 221617503,5-Bis(phenylmethoxy)-alpha-[[(phenylmethyl)[6-[[6-(2-pyridinyl)hexyl]-oxy]hexyl]amino]methyl]benzenemethanolAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 1-[3,5-bis(phenylmethoxy)phenyl]-2-bromoethanone (1.76 g) in dry DMF (15 ml) was added dropwise to a solution of N-[6-[[6-(2-pyridinyl)hexyl]oxy]hexyl]benzenemethanamine (1.58 g) and DEA (0.56 g) in dry DMF (15 ml) under nitrogen. The mixture was stirred at room temperature for 4.5 h, and the solvent was evaporated. Sodium borohydride (1.75 g) was added portionwise to the ice-cooled solution of the residue in ethanol (40 ml) under nitrogen and the reaction mixture was stirred at room temperature for 16 h and concentrated. The residue was partitioned between ethyl acetate (70 ml) and water (70 ml), the organic layer was washed with brine (70 ml), dried and concentrated to give an oil which was purified by FCC eluting with ethyl acetatehexane-triethylamine (25:75:1) to give the title compound as a colourless oil (2.00 g), t.l.c. (ethyl acetate-hexane (1:2)+ few drops triethylamine) Rf 0.19.

Aufarbeitung

  1. customthe solvent was evaporated
  2. additionSodium borohydride (1.75 g) was added portionwise to the ice-
  3. temperaturecooled solution of the residue in ethanol (40 ml) under nitrogen
  4. stirringthe reaction mixture was stirred at room temperature for 16 h
  5. concentrationconcentrated
  6. customThe residue was partitioned between ethyl acetate (70 ml) and water (70 ml)
  7. washthe organic layer was washed with brine (70 ml)
  8. customdried
  9. concentrationconcentrated
  10. customto give an oil which
  11. customwas purified by FCC
  12. washeluting with ethyl acetatehexane-triethylamine (25:75:1)

Quellen und Nachweise

ORD-Eintrag
ord-cd9e1e2e5167445280df59ea99966096
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04963564

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