Sulfuric Acid → HCID 53354755, compound

Temperature

95 °C

7-Methyl-2-phenyl-N-(propan-2-ylidene)-2H-benzo[b][1,4]oxazin-4(3H)-amine (1.3 g) and N-methyl piperidone (0.629 g) were dissolved in dioxane (2 mL). To this mixture was added 7% H2SO4 in Dioxane (25 mL) and the resulting reaction mixture was heated at 95° C. for 2 h. Reaction was monitored by TLC. After completion of reaction, the mixture was concentrated under reduced pressure, and the residue basified with NaOH solution to pH 12. The mixture was extracted with EtOAc (3×100 mL), and the organic layer dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography using silica (100-200 mesh size) using 3% MeOH/DCM as eluent. The purified compound was further purified using preparative TLC using 5% MeOH/DCM as mobile phase to obtain pure product as a light brown solid (0.08 g). 1H NMR (CD3OD, HCl Salt): d (ppm): 7.56 (d, 2H), 7.42 (m, 3H), 6.90 (s, 1H), 6.56 (s, 1H), 5.32 (m, 1H), 4.70 (m, 1H), 4.50 (m, 1H), 4.38 (m, 1H), 4.05 (m, 1H), 3.82 (m, 1H), 3.58 (m, 1H), 3.20 (m, 2H), 3.10 (s, 3H), 2.40 (s, 3H).

1. customthe resulting reaction mixture
2. customReaction
3. customAfter completion of reaction
4. concentrationthe mixture was concentrated under reduced pressure
5. extractionThe mixture was extracted with EtOAc (3×100 mL)
6. dry with materialthe organic layer dried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe crude product was purified by column chromatography
9. customThe purified compound was further purified

ORD record

ord-804abbcb63084cb78355f0300671d5fa

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193728B2