Hydrochloric Acid → 4-(5-Bromoindolin-1-yl)cyclohexanone

HRID 1922515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922515
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:20][CH2:19][C:14]3(OCC[O:15]3)[CH2:13][CH2:12]1)[CH2:6][CH2:5]2.Cl>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:12][CH2:13][C:14](=[O:15])[CH2:19][CH2:20]1)[CH2:6][CH2:5]2

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 585053135-Bromo-1-(1,4-dioxaspiro[4.5]decan-8-yl)indoline

Produkt 1

HCID 598070744-(5-Bromoindolin-1-yl)cyclohexanoneAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of compound 4 (4.0 g, 11.83 mmol) in acetone (50 mL) was treated with 10% HCl solution (50 mL) and the resulting mixture was stirred for over night (16 h). Acetone was evaporated, crude was basified with 2 N NaOH solution and product was extracted into CH2Cl2 (3×25 mL). The combined CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated and the crude product was purified by column chromatography on silica gel (ethyl acetate:hexanes, 1:4) to obtain compound 5 (2.9 g, 83%) as a solid. 1H NMR (CDCl3) δ 7.15 (d, J=6.6 Hz, 2H), 6.32 (d, J=8.7 Hz, 1H), 3.81 (tt, J=7.2, 23.4 Hz, 1H), 3.37 (t, J=16.8 Hz, 2H), 2.95 (t, J=16.5 Hz, 2H), 2.51-2.41 (m, 4H), 2.18-2.11 (m, 2H), 1.92-1.78 (m, 2H). MS-ESI (m/z, %): 296 (96), 294 (M+, 100), 200 (30).

Aufarbeitung

  1. customAcetone was evaporated
  2. extractionwas extracted into CH2Cl2 (3×25 mL)
  3. washThe combined CH2Cl2 layer was washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe crude product was purified by column chromatography on silica gel (ethyl acetate:hexanes, 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-dc6c85701d9e4229b65649a5c22abca5
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173813B2

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