Potassium Iodide → 1-(3-(10,11-dihyd ro-5 H-dibenz[b,f]azepin-5-yl)-1-propyl)-2-methyl-3-piperidinecarboxylic acid methyl ester

HRID 363312

反応式

HRID 363312 の反応式
[I-].[K+].Cl[CH2:4][CH2:5][CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:29][O:30][C:31]([CH:33]1[CH2:38][CH2:37][CH2:36][NH:35][CH:34]1[CH3:39])=[O:32]>C(C(C)=O)C>[CH3:29][O:30][C:31]([CH:33]1[CH2:38][CH2:37][CH2:36][N:35]([CH2:4][CH2:5][CH2:6][N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][CH2:10][C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]2=3)[CH:34]1[CH3:39])=[O:32]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2867795-(3-Chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepineHCID 51358493Methyl 2-methylpiperidine-3-carboxylate hydrochloride

生成物 1

HCID 544771091-(3-(10,11-dihyd ro-5 H-dibenz[b,f]azepin-5-yl)-1-propyl)-2-methyl-3-piperidinecarboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒2 回

実験手順

A mixture of potassium iodide (17.5 g, 0.11 mol) and methyl ethyl ketone (180 ml) was heated at reflux temperature for 1 h. A solution of 5-(3-chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine (4.8 g, 0.019 mol, prepared similarly as described in example 1) in methyl ethyl ketone (25 ml) was added and heating at reflux temperature was continued for 2 h. Potassium carbonate (8.5 g, 0.061 mol) and 2-methyl-3-piperidinecarboxylic acid methyl ester hydrochloride (5.1 g, 0.026 mol) were added and the reaction mixture was heated just below reflux temperature for 64 h. After cooling, the reaction mixture was filtered (Hyflo) and the solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica gel (275 g) using a mixture of heptane and ethyl acetate (1:1) as eluent, to give 3.4 g of 1-(3-(10,11 -dihydro-5H-dibenz[b,f]-azepin-5-yl)-1-propyl)-2-methyl-3-piperidinecarboxylic acid methyl ester as an oil.

後処理

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 h
  3. additionwas added
  4. temperatureheating
  5. temperatureat reflux temperature
  6. temperaturethe reaction mixture was heated just
  7. temperaturebelow reflux temperature for 64 h
  8. temperatureAfter cooling
  9. filtrationthe reaction mixture was filtered (Hyflo)
  10. customthe solvent was evaporated in vacuo
  11. customThe residue was purified by flash chromatography on silica gel (275 g)
  12. additiona mixture of heptane and ethyl acetate (1:1) as eluent

出典と根拠

ORDレコード
ord-4a3adc4d803e43d386a0a4b565f109ab
出典データセット
uspto-grants-1999_02
特許番号
US05874428

関連ノート

読み込み中…