Water → 4,6-dimethyl-N-(alpha-phenylethyl)phenoxazine

HRID 1381660Notes

Reaction equation

HRID 1381660 reaction equation
[C:1]1([CH:7]([N:9]2[C:22]3[CH:21]=CC=C[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])[CH2:24][CH2:25][CH3:26].[CH3:28]I.O>O1CCCC1.CCCCCC>[CH3:26][C:25]1[C:17]2[O:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[CH3:28])[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:23][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14031257N-alpha-PhenylethylphenoxazineHCID 178418339Butyllithium

Product 1

HCID 143402314,6-dimethyl-N-(alpha-phenylethyl)phenoxazine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 10 g (34 mmoles) of N-(α-phenylethyl)phenoxazine in 100 ml of anhydrous tetrahydrofuran, under nitrogen, was cooled to -78° C. in a dry ice-acetone bath. 82 ml of a 1.4N solution (114 mmoles) of n-butyl lithium in hexane was slowly added to the cold solution while the temperature was maintained below 0° C. When the addition was completed, the reaction mixture was stirred for 4 hours at 0° C. Then 10.8 g (76 mmoles) of methyl iodide were added, the temperature was maintained at 0°-5° C. The resulting mixture was stirred for 16 hours at 0° C. and then poured into water and extracted with ethyl acetate (3.1 l). The combined extracts were dried and the solvent was removed. The residue purified by column chromatography on 450 g of silica gel, using hexane as eluant afford the pure 4,6-dimethyl-N-(α-phenylethyl)phenoxazine, as an oil, ir: 3837, 2940, 1640, 1600, 1570, 1470 cm-1 : nmr: (CDCl3) 1.90-1.83 ppm (d, 3H), 2.23 ppm (s, 6H), 5.20 ppm (c, 1H), 6.40-6.16 ppm (m, 2H), 6.80-6.53 ppm (m, 4H), 7.53-7.20 ppm (m, 5H).

Workup

  1. temperaturewas maintained below 0° C
  2. additionWhen the addition
  3. temperaturethe temperature was maintained at 0°-5° C
  4. stirringThe resulting mixture was stirred for 16 hours at 0° C.
  5. extractionextracted with ethyl acetate (3.1 l)
  6. customThe combined extracts were dried
  7. customthe solvent was removed
  8. customThe residue purified by column chromatography on 450 g of silica gel

Sources & evidence

ORD record
ord-f473e8a40139425cab5c1d0b6e7079b6
Source dataset
uspto-grants-1989_02
Patent number
US04803269

Reaction notes

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