HCID 22735207, Verbindung → 3-(2-(Benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine

HRID 50594

Reaktionsgleichung

Reaktionsgleichung von HRID 50594
[CH:1]([N:4]([CH:30]([CH3:32])[CH3:31])[C:5](=O)[CH2:6][CH:7]([C:14]1[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:15]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1>O1CCCC1>[CH2:22]([O:21][C:15]1[CH:16]=[CH:17][C:18]([Br:20])=[CH:19][C:14]=1[CH:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH:30]([CH3:32])[CH3:31])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

4

Edukt 2

HCID 22735207HCID 22735207, VerbindungHCID 68718528lithium aluminium hydride THF

Produkt 1

HCID 129724153-(2-(Benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amineAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of (±)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropionamide (11.8 g) in 40 ml of dry tetrahydrofuran was added 1 M lithium aluminium hydride/tetrahydrofuran (36 ml). The reaction was refluxed for 4 hrs and then quenched with the dropwise addition of water. After removal of the precipitate the solvent was evaporated and the oily residue dissolved in diluted sulphuric acid. The aqueous phase was washed several times with diethyl ether, adjusted to pH 10-12 (aqueous NaOH), and extracted with diethyl ether. The extract was dried (sodium sulphate), filtered and evaporated to dryness in vacuum to leave 8.1 g (76.7%) of the title compound as a viscous colourless oil, tlc: (4) 0.86. The NMR spectrum corresponds to the product, obtained from the tosylate precursor (see above).

Aufarbeitung

  1. temperatureThe reaction was refluxed for 4 hrs
  2. customquenched with the dropwise addition of water
  3. customAfter removal of the precipitate the solvent
  4. customwas evaporated
  5. dissolutionthe oily residue dissolved in diluted sulphuric acid
  6. washThe aqueous phase was washed several times with diethyl ether
  7. extractionextracted with diethyl ether
  8. dry with materialThe extract was dried (sodium sulphate)
  9. filtrationfiltered
  10. customevaporated to dryness in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9de1c56752b94d8094457e8551914fca
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713464B1

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