Sodium hydride → N,N-Dimethyl-3-{2-[4-(2-methoxyphenyl)butyl]phenoxy}propylamine

HRID 743208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 743208
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19].[H-].[Na+].Cl.[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27]Cl>CC(N(C)C)=O>[CH3:23][N:24]([CH2:25][CH2:26][CH2:27][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][CH2:11][CH2:10][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH3:29]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 194239792-[4-(2-Methoxyphenyl)butyl]phenol

Produkt 1

HCID 19423881N,N-Dimethyl-3-{2-[4-(2-methoxyphenyl)butyl]phenoxy}propylamineAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

Following a procedure similar to that described in Example 2(a), 200 mg of 2-[4-(2-methoxyphenyl)butyl]phenol (prepared as described in Preparation 4), 75 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) and 0.14 g of 3-dimethylaminopropyl chloride hydrochloride were reacted in 20 ml of dimethylacetamide. The crude product, extracted as described in Example 2(a), was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 227 mg (yield 85%) of the title compound as pale yellow solid.

Aufarbeitung

  1. extractionThe crude product, extracted
  2. customwas purified by column chromatography through silica gel
  3. additionby volume mixture of methylene chloride and methanol as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-79e7a6ecc7db4a0083533a7b5786e19a
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556864

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