Water → 4-methyl-N-(alpha-phenylethyl)phenoxazine

HRID 247377Notes

Reaction equation

[C:1]1([CH:7]([N:9]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:16][C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23]([Li])CCC.CI.O>O1CCCC1.CCCCCC>[CH3:23][C:18]1[C:17]2[O:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH3:8])[C:22]=2[CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: -20 °C

Procedure

2.87 g (10 mmoles) of N-(α-phenylethyl)phenoxazine were dissolved, under nitrogen atmosphere, in 100 ml of dry tetrahydrofuran. The solution was cooled to -20° C. and 7.2 ml of a 1.67N solution of n-butyllithium (12 mmoles) in hexane was added thereto. The resulting mixture was stirred for 1 hour at -20° C. and then treated with 1.7 g (12 mmoles, 0.74 ml) of methyl iodide. Stirring was continued for an additional hour at the same temperature. The reaction solution was then poured into water (200 ml) and extracted with ethyl acetate (2×50 ml). The combined extracts were dried over sodium sulfate and the solvent removed under reduced pressure. The oily residue (2.96 g) was purified by thin layer chromatography (TLC) using hexane as solvent, to yield 4-methyl-N-(α-phenylethyl)phenoxazine, as an oil: ir: 2925; 2875; 1603 cm-1 ; nmr: (CDCl3) 1.80 ppm (d, 3H), 2.23 ppm (s, 3H), 7.17 ppm (c, 1H), 6.20-6.80 ppm (m, 7H), 7.60 ppm (m, 5H).

Workup

stirringStirring
waitwas continued for an additional hour at the same temperature
extractionextracted with ethyl acetate (2×50 ml)
dry with materialThe combined extracts were dried over sodium sulfate
customthe solvent removed under reduced pressure
customThe oily residue (2.96 g) was purified by thin layer chromatography (TLC)

Sources & evidence

ORD record: ord-fa85d35abca345e2bec4ad63169e6270
Source dataset: uspto-grants-1987_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04707473

Reaction notes

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