Sodium Iodide → (4-Bromo-3-methyl-phenyl)-(2-morpholin-4-yl-ethyl)-amine

HRID 2216147

反応式

HRID 2216147 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].Cl[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CS(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:4][C:3]=1[CH3:9]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 233594-Bromo-3-methylanilineHCID 767274-(2-Chloroethyl)morpholine

生成物 1

HCID 21886410(4-Bromo-3-methyl-phenyl)-(2-morpholin-4-yl-ethyl)-amine収率 32.5%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-Bromo-3-methylaniline (0.96 gm, 5.14 mmol), 4-(2-chloro-ethyl)-morpholine (1 gm, 5.4 mmol), K2CO3 (1.5 gm, 10.8 mmol), and NaI (0.81 gm, 5.4 mmol) were suspended in DMSO (10 mL) and the mixture was stirred vigorously at reflux for 12 h. The mixture was cooled, diluted with EtOAc, and washed with saturated NaHCO3. The organic layer was washed with another portion of NaHCO3, brine (50 mL), and was dried over MgSO4. Removal of the solvents in vacuo followed by flash chromatography of the residue (Biotage Flash System—40 M SiO2 column, 10% EtOAc in hexanes to 100% EtOAc) yielded the product (500 mg, 31%) as a tan oil. 1H-NMR (CDCl3; 400 MHz): δ 7.36 (d, 1H, J=8.6 Hz), 6.61 (d, 1H, J=2.8 Hz), 6.43 (dd, 1H, d, 8.6, 2.8 Hz), 4.36 (br s, 1H), 3.80 (t, 4H, J=4.6 Hz), 3.20 (t, 2H, J=5.8 Hz), 2.69 (t, 2H, J=6.0 Hz), 2.54 (t, 4H, J=4.4 Hz), 2.40 (s, 3H). ESI-MS (m/z): Calcd. for C13H19BrN2O: 299.2; found: 299.1, 301.1.

後処理

  1. temperatureat reflux for 12 h
  2. temperatureThe mixture was cooled
  3. washwashed with saturated NaHCO3
  4. washThe organic layer was washed with another portion of NaHCO3, brine (50 mL)
  5. dry with materialwas dried over MgSO4
  6. customRemoval of the solvents in vacuo

出典と根拠

ORDレコード
ord-15729a239ab343ad8f79f5cbbe49cfc9
出典データセット
uspto-grants-2006_09
特許番号
US07109354B2

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