Ethylamine → N'-(6-Chloro-2-methyl-phenyl)-N-ethyl-propane-1,3-diamine

HRID 1250898

Reaktionsgleichung

Reaktionsgleichung von HRID 1250898
[CH2:1]([NH2:3])[CH3:2].[Cl:4][C:5]1[C:10]([NH:11][CH2:12][CH2:13][CH2:14]O)=[C:9]([CH3:16])[CH:8]=[CH:7][CH:6]=1>O1CCCC1.ClCCl>[Cl:4][C:5]1[C:10]([NH:11][CH2:12][CH2:13][CH2:14][NH:3][CH2:1][CH3:2])=[C:9]([CH3:16])[CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 2

HCID 6341EthylamineHCID 183248341-(6-Chloro-2-methyl-phenyl)amino-3-hydroxy-propane

Produkt 1

HCID 18324822N'-(6-Chloro-2-methyl-phenyl)-N-ethyl-propane-1,3-diamineAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of a 2.0 M solution of ethylamine in tetrahydrofuran (139.5 mL) and the hydrobromide salt of Example 12, Step A (9.5 g) was stirred at ambient temperature under nitrogen for 48 hours. The tetrahydrofuran was removed in vacuo and the residue was partitioned between dichloromethane and 1N sodium hydroxide. The extracts were washed with brine, dried over sodium sulfate, and concentrated in vacuo to give a brown oil. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with a solvent gradient (from 95:5 to 80:20 dichloromethane-methanol containing 0.2% ammonium hydroxide) gave the title compound (3.4 g, 54.3%) as a yellow oil, which was used as such in the next step.

Aufarbeitung

  1. customThe tetrahydrofuran was removed in vacuo
  2. customthe residue was partitioned between dichloromethane and 1N sodium hydroxide
  3. washThe extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil
  7. customabsorbed onto a column of Merck-60 flash silica gel
  8. washElution with a solvent gradient (from 95:5 to 80:20 dichloromethane-methanol containing 0.2% ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag
ord-87b31028294e4602931608be0f5cbc66
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06340687B1

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