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Hydrochloric Acid → 5-((4-Bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoic acid

HRID 2222827
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2222827
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:14])=[CH:5][CH:4]=1.[OH-].[Na+].Cl.C(=O)([O-])[O-:21].[Na+].[Na+].[Br:26][C:27]1[CH:28]=[CH:29][C:30](F)=[C:31]([CH:34]=1)[CH:32]=[O:33]>CS(C)=O>[Br:26][C:27]1[CH:28]=[CH:29][C:30]([N:8]([CH2:7][C:6]2[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:13][CH2:12][CH2:11][CH2:10][C:9]([OH:21])=[O:14])=[C:31]([CH:32]=[O:33])[CH:34]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric Acid2×HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 115068011-(4-Methoxybenzyl)piperidin-2-one

Produkt 1

HCID 114954475-((4-Bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoic acid
Ausbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 1-(4-methoxybenzyl)piperidin-2-one (50.0 g) was added aqueous 4N sodium hydroxide solution (228 ml) and then the mixture was refluxed for a day. The mixture was cooled to 0° C. and concentrated hydrochloric acid (76 ml) was added thereto. The mixture was neutralized. Then, after adding sodium carbonate (53.8 g) and dimethyl sulfoxide (600 ml), 5-bromo-2-fluorobenzaldehyde (38.6 g) was added dropwise at 135° C. to the mixture. After refluxing for 5 hours, the mixture was neutralized with 3N hydrochloric acid at 0° C., and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, after which it was dried with magnesium sulfate. The solvent was distilled off under reduced pressure to give 5-((4-bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoic acid (77.2 g) as a brown oily material.

Aufarbeitung

  1. temperaturethe mixture was refluxed for a day
  2. additionwas added dropwise at 135° C. to the mixture
  3. temperatureAfter refluxing for 5 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialafter which it was dried with magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d6f9e368feba41e8bd1d3cefd6be44f3
Quelldatensatz
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07371772B2

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