Imidazole → 2-Cyanomethyl-1,2,3,4-tetrahydroquinoline

HRID 862561

反応式

HRID 862561 の反応式
O[CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4]1.[NH:13]1C=CN=[CH:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.S([O-])([O-])(=O)=S.[Na+].[Na+].[C-]#N.[Na+]>C1(C)C=CC=CC=1.C(#N)C>[C:14]([CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4]1)#[N:13]

参加物

8

反応物 6

HCID 795ImidazoleHCID 807IodineHCID 8929Sodium CyanideHCID 11776TriphenylphosphineHCID 24477Sodium ThiosulfateHCID 15052240(1,2,3,4-Tetrahydroquinolin-2-yl)methanol

生成物 1

HCID 5834192-Cyanomethyl-1,2,3,4-tetrahydroquinoline収率 94%

試薬・触媒・溶媒 1

HCID 21584213Acetonitrile toluene溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-hydroxymethyltetrahydroquinoline (35.9 g, 0.22 mol), imidazole (35.95 g, 0.528 mol), and triphenylphosphine (69.24 g, 0.264 mol) in a mixed solvent of 5:1 toluene/acetonitrile (750 mL) was added iodine (61.42 g, 0.242 mol) at 0° C. The mixture was stirred for 15 min at 0° C. and for 30 min at room temperature. Aqueous sodium thiosulfate solution (200 mL) was added. The organic layer was separated, washed with brine, dried over magnesium sulfate, and concentrated. The residue was triturated with diethyl ether and the insoluble materials were removed by filtration. The filtrate was concentrated and the residual oil was dissolved in DMF (200 mL). To the solution was added sodium cyanide (43.2 g, 0.881 mol) and the mixture was heated at 80° C. for 10 h. The resulting mixture was poured into ice-water and extracted with a mixture of toluene and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 1:1 hexane/dichloromethane to 100% dichloromethane as eluents to give 31.6 g of the title compound (94%).

後処理

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was triturated with diethyl ether
  6. customthe insoluble materials were removed by filtration
  7. concentrationThe filtrate was concentrated
  8. dissolutionthe residual oil was dissolved in DMF (200 mL)
  9. temperaturethe mixture was heated at 80° C. for 10 h
  10. extractionextracted with a mixture of toluene and ethyl acetate
  11. washThe organic layer was washed with brine
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated
  14. customThe residue was purified by silica gel column chromatography with 1:1 hexane/dichloromethane to 100% dichloromethane as eluents

出典と根拠

ORDレコード
ord-b02b8705a4b848629461a5fc303bd891
出典データセット
uspto-grants-1998_02
特許番号
US05719152

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