m-Tolylisothiocyanate → 5-benzyl-1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine

HRID 8722

反応式

HRID 8722 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](OCC)(OCC)[CH:10]([NH2:20])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([CH3:30])[CH:26]=[CH:25][CH:24]=[C:23]([N:27]=[C:28]=S)[CH:22]=1>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2[N:27]([C:23]3[CH:22]=[C:21]([CH3:30])[CH:26]=[CH:25][CH:24]=3)[CH:28]=[N:20][C:10]=2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 69304m-TolylisothiocyanateHCID 217299351-Benzyl-4,4-diethoxypiperidin-3-amine

生成物 1

HCID 219836255-benzyl-1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine収率 74.9%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A solution of 1-benzyl-4,4-diethoxy-piperidin-3-ylamine 16 (600 mg, 2.2 mmol), and m-tolyl isothiocyanate (328 mg, 2.2 mmol) in 10 mL chloroform was heated at 60° C. for 2 hr. The solvent was removed in vacuo, and the residue was treated with 10 mL each of 10% hydrochloric acid and dioxane and heated at reflux for 1 h. After removal of the solvent the residue was dissolved in 50 mL ethanol followed by addition of Raney Nickel (ca. 3.0 g). The suspension was heated at reflux for 2 h then allowed to cool to room temperature. The solids were removed by filtration. The solvent was evaporated in vacuo, and the residue was diluted with 10% sodium hydroxide solution and extracted into chloroform. The organic layer was dried over potassium carbonate, filtered and concentrated to provide 500 mg of 5-benzyl-1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine 17a as a light brown oil, [M+H]+=304.

後処理

  1. customThe solvent was removed in vacuo
  2. additionthe residue was treated with 10 mL each of 10% hydrochloric acid and dioxane
  3. temperatureheated
  4. temperatureat reflux for 1 h
  5. customAfter removal of the solvent the residue
  6. dissolutionwas dissolved in 50 mL ethanol
  7. additionfollowed by addition of Raney Nickel (ca. 3.0 g)
  8. temperatureThe suspension was heated
  9. temperatureat reflux for 2 h
  10. customThe solids were removed by filtration
  11. customThe solvent was evaporated in vacuo
  12. additionthe residue was diluted with 10% sodium hydroxide solution
  13. extractionextracted into chloroform
  14. dry with materialThe organic layer was dried over potassium carbonate
  15. filtrationfiltered
  16. concentrationconcentrated

出典と根拠

ORDレコード
ord-43a2b6c9e1a140b48fd022c4ada43800
出典データセット
uspto-grants-2006_08
特許番号
US07091200B2

関連ノート

読み込み中…