Hydrogen Bromide → 5-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one

HRID 544716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 544716
[Cl:1][C:2]1[C:3]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:4][C:5]([O:12]C)=[C:6]([CH2:8][C:9]([OH:11])=O)[CH:7]=1.Br.C(=O)(O)[O-].[Na+].ClC1C(N2CCCCC2)=CC(O)=C(CC(O)=O)C=1>O>[Cl:1][C:2]1[C:3]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:4][C:5]2[O:12][C:9](=[O:11])[CH2:8][C:6]=2[CH:7]=1

Komponenten

6

Edukt 4

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 539130445-Chloro-2-hydroxy-4-(piperidin-1-yl)-phenylacetic acidHCID 541834705-Chloro-2-methoxy-4-(piperidin-1-yl)-phenylacetic acid

Produkt 1

HCID 135769525-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 8.5 g (30 mmoles) of 5-chloro-2-methoxy-4-(piperidin-1-yl)-phenylacetic acid in 150 ml of 48% strength hydrobromic acid is boiled under reflux for 15 hours. The reaction mixture is cooled, diluted with water and adjusted to a pH of 3-4 with saturated sodium bicarbonate solution. The mixture is then extracted with ethyl acetate, and the combined organic phases are washed with water, dried over sodium sulphate and concentrated by evaporation in a high vacuum rotary evaporator. There is obtained a dark-grey foam comprising 5-chloro-2-hydroxy-4-(piperidin-1-yl)-phenylacetic acid, which is reacted, without being purified, to form 5-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one.

Aufarbeitung

  1. temperatureunder reflux for 15 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionThe mixture is then extracted with ethyl acetate
  4. washthe combined organic phases are washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation in a high vacuum rotary evaporator
  7. customThere is obtained a dark-grey foam
  8. customis reacted
  9. customwithout being purified

Quellen und Nachweise

ORD-Eintrag
ord-19aeba0b3f9041678e987c65c40cc3bb
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04451462

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