Potassium Hydroxide → 5-Tert-butyl-4-(2-dimethylamino-ethoxy)-2-methyl-phenylamine

HRID 1446691

Reaktionsgleichung

Reaktionsgleichung von HRID 1446691
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:3]=1.Br.[CH2:15](Br)[CH3:16].[CH3:18][NH:19][CH3:20].[OH-].[K+]>COCCOC>[C:10]([C:4]1[C:5]([O:9][CH2:16][CH2:15][N:19]([CH3:20])[CH3:18])=[CH:6][C:7]([CH3:8])=[C:2]([NH2:1])[CH:3]=1)([CH3:13])([CH3:12])[CH3:11]

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 4251824-Amino-2-tert-butyl-5-methyl-phenolHCID 19354026N,N-dimethylamine ethyl bromide HBr salt

Produkt 1

HCID 685443235-Tert-butyl-4-(2-dimethylamino-ethoxy)-2-methyl-phenylamineAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Heat a mixture of 4-amino-2-tert-butyl-5-methyl-phenol (600 mg, 3.2 mmol), N,N-dimethylamine ethyl bromide HBr salt (820 mg, 3.4 mmol), and potassium hydroxide (750 mg, 13.4 mmol) in 1,2-dimethoxyethane in a microwave vessel with irradiation of <10 Watts at a temperature of 150-170° C. for 5 minutes. After the reaction cools, filter via Celite® and wash with dichloromethane. Concentrate the filtrate and purify by silica gel column chromatography, with a gradient from 100% DCM to 5% MeOH in DCM to 5% (2N ammonia in MeOH) in DCM to yield the title compound as a red brown oil (26% yield). LCMS (ES), m/z 251 (M+1).

Aufarbeitung

  1. temperatureHeat
  2. customwith irradiation of <10 Watts at a temperature of 150-170° C. for 5 minutes
  3. filtrationfilter via Celite®
  4. washwash with dichloromethane
  5. concentrationConcentrate the filtrate
  6. custompurify by silica gel column chromatography, with a gradient from 100% DCM to 5% MeOH in DCM to 5% (2N ammonia in MeOH) in DCM

Quellen und Nachweise

ORD-Eintrag
ord-23c888667c20442baa1460856fd5d581
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666879B2

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