N-bromobutanimide → HCID 59807078, Verbindung

HRID 1922521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922521
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:14][CH2:13][CH2:12]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[Br:21]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[N:11]([CH:8]1[CH2:7][CH2:6][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:10][CH2:9]1)[CH2:12][CH2:13][CH2:14]2

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 598070451-(1,4-Dioxaspiro[4.5]decan-8-yl)-1,2,3,4-tetrahydroquinoline

Produkt 1

HCID 59807078HCID 59807078, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of compound 3 (0.19 g, 0.695 mmol) in dry DMF (3 mL) was treated with N-bromosuccinimide (0.124 g, 0.695 mmol) in DMF (2 mL) at 0° C. over a period of 10 minutes. The reaction was stirred at the same temperature for 3.5 h. The reaction was diluted with water (50 mL) and the product was extracted into ethyl acetate (2×20 mL). The combined ethyl acetate layer was washed with water (2×20 mL), brine (15 mL) and dried (Na2SO4). Solvent was evaporated and the crude mixture was purified by column chromatography on silica gel (ethyl acetate:hexanes, 1:9) to obtain compound 4 (0.225 g, 92%) as a syrup. 1H NMR (CDCl3) δ 7.16-7.05 (m, 2H), 6.60-6.52 (m, 1H), 3.96 (s, 4H), 3.64-3.55 (m, 1H), 3.20 (t, 2H, J=5.7 Hz), 2.69 (t, 2H, J=6.0 Hz), 1.91-1.54 (m, 10H); ESI-MS (m/z, %): 352, 354 (MH+, 100).

Aufarbeitung

  1. extractionthe product was extracted into ethyl acetate (2×20 mL)
  2. washThe combined ethyl acetate layer was washed with water (2×20 mL), brine (15 mL)
  3. dry with materialdried (Na2SO4)
  4. customSolvent was evaporated
  5. customthe crude mixture was purified by column chromatography on silica gel (ethyl acetate:hexanes, 1:9)

Quellen und Nachweise

ORD-Eintrag
ord-603cfcf43bdf4079b528e75c7c48a2e0
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173813B2

Notizen zur Reaktion

Wird geladen…