Diethylamine → 10-(3'-Diethylaminopropyl)phenoxazine

HRID 1491588Notes

Reaction equation

HRID 1491588 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:12][C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.C([O-])([O-])=O.[K+].[K+].[CH2:25]([NH:27][CH2:28][CH3:29])[CH3:26]>C(#N)C.O>[CH2:25]([N:27]([CH2:28][CH3:29])[CH2:2][CH2:3][CH2:4][N:5]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:12][C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH3:26]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 1008392610-(3-Chloropropyl)-10H-phenoxazine

Product 1

HCID 1040233310-(3'-Diethylaminopropyl)phenoxazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1 g (4.31 mmol) of the product of Example 1 was dissolved in 150 mL of anhydrous acetonitrile, and 1.5 g KI, 2.13 g K2CO3 and 1.6 mL (15.4 mmol) of N,N-diethylamine were added. The mixture was refluxed overnight until a substantial amount of product was formed (TLC, System B, Rf =0.40). The reaction mixture was diluted with water and extracted with ether three times. The ether layer was washed with water and dried over anhydrous Na2SO4 and evaporated. The crude oil was subjected to column chromatography for purification. Ethylacetate-petroleum ether (50 mL+50 mL) eluted the title compound as the free base as a colorless oil, which was dried and used for NMR studies. An ethereal solution of the free base was treated with an excess of tartaric acid to separate the hygroscopic tartrate salt (1.2 g). UV-λmax (MeOH) 215, 238 and 320 nm; IR (CHCl3) 3378, 2974, 2838, 1453, 1375, 1155, 973 and 722 cm-1 ; 1H-NMR (`δ`) 6.51-6.80 (m, 8H, ArH, H1 -H4 and H6 -H9), 1.16 (t, 6H, Hc and Hd), 1.70 (m, 2H, H1), 2.50 (q, 4H, Ha and Hb, J=7 Hz), 3.42-3.63 (m, 4H, Hk and Hm); 13C-NMR 111.54 (C1 and C9), 115.49 (C4 and C6), 121.21 (C3 and C7), 123.85 (C2 and C8), 132.72 (C1' and C9'), 144.95 (C4' and C6'), 8.21 (Cc and Cd), 19.90 (C1), 40.72 (Ca and Cb), 45.87 (Cm), and 48.50 (Ck); EIMS (m/z) 296 (M+).

Workup

  1. temperatureThe mixture was refluxed overnight until a substantial amount of product
  2. customwas formed (TLC, System B, Rf =0.40)
  3. extractionextracted with ether three times
  4. washThe ether layer was washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated
  7. customThe crude oil was subjected to column chromatography for purification
  8. washEthylacetate-petroleum ether (50 mL+50 mL) eluted the title compound as the free base as a colorless oil, which
  9. customwas dried
  10. additionAn ethereal solution of the free base was treated with an excess of tartaric acid
  11. customto separate the hygroscopic tartrate salt (1.2 g)

Sources & evidence

ORD record
ord-beb8de64dadf4f97a77317478e52ae80
Source dataset
uspto-grants-1994_12
Patent number
US05371081

Reaction notes

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