Dimethylamine, hydrochloride → 3-(4-bromophenyl)-N,N-dimethylpropanamide

HRID 230624

Reaktionsgleichung

Reaktionsgleichung von HRID 230624
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[C:13](N1C=CN=C1)([N:15]1C=CN=[CH:16]1)=O.Cl.CNC.C(N(C(C)C)CC)(C)C>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:15]([CH3:16])[CH3:13])=[O:12])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 10473Dimethylamine, hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 27356093-(4-Bromophenyl)propionic acid

Produkt 1

HCID 577628213-(4-bromophenyl)-N,N-dimethylpropanamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-(4-bromophenyl)propionic acid (1.0 g, 4.37 mmol) in dichloromethane (30 ml) was treated in one portion with solid 1,1′-carbonyldiimidazole (707 mg, 4.36 mmol). This mixture was allowed to stir at room temperature for 15 minutes. Dimethylamine hydrochloride (360 mg, 4.42 mmol) was then added followed by diisopropylethylamine (0.76 ml, 4.4 mmol) and the stirring continued for 1 hour at room temperature. The reaction mixture was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic layer was dried over sodium sulphate and evaporated under reduced pressure to give the title compound as a colourless oil (972 mg, 87%).

Aufarbeitung

  1. waitthe stirring continued for 1 hour at room temperature
  2. customThe reaction mixture was partitioned between dichloromethane and saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5afa863fe97e47039bb77d383870622a
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566735B2

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