Diethylamine → 10-(3'-Diethylaminopropyl)phenoxazine

HRID 1491588ノート

反応式

HRID 1491588 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 1040233310-(3'-Diethylaminopropyl)phenoxazine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-beb8de64dadf4f97a77317478e52ae80
出典データセット
uspto-grants-1994_12
特許番号
US05371081

反応ノート

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