Potassium Iodide → 3-(4-Cyano-4-phenylpiperidin-1-yl)propylphthalimide

HRID 278921

反応式

HRID 278921 の反応式
Cl.[C:2]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)#[N:3].Br[CH2:17][CH2:18][CH2:19][C:20]1[CH:30]=[CH:29][CH:28]=[C:22]2[C:23]([NH:25][C:26](=[O:27])[C:21]=12)=[O:24].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[C:2]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:6][N:7]([CH2:17][CH2:18][CH2:19][C:20]2[CH:30]=[CH:29][CH:28]=[C:22]3[C:23]([NH:25][C:26](=[O:27])[C:21]=23)=[O:24])[CH2:8][CH2:9]1)#[N:3]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 30849734-Phenylpiperidine-4-carbonitrile hydrochlorideHCID 21958088Bromopropylphthalimide

生成物 1

HCID 227252233-(4-Cyano-4-phenylpiperidin-1-yl)propylphthalimide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
105 °C

実験手順

A mixture of 4-cyano-4-phenylpiperidine hydrochloride (111 g, 0.5 mol), 3-bromopropylphthalimide (135.39 g, 0.505 mol), potassium carbonate (276.42 g, 2 mol), and potassium iodide (5.4 g) in DMF (1 L) was stirred and heated at 100-110 ° C. for 8 hours. About 80% of the solvent was evaporated at reduced pressure, the residue was diluted with dichloromethane (1 L) and washed with brine (3×300 mL) and dried (Na2SO4). Solvent was evaporated from the dichloromethane solution and the residue was treated with isopropanol (400 mL) and cooled. The pale yellow crystalline product formed was filtered, washed with ice-cold isopropanol and dried (168.6 g, 90%); M.p. 96-98° C.

後処理

  1. customAbout 80% of the solvent was evaporated at reduced pressure
  2. additionthe residue was diluted with dichloromethane (1 L)
  3. washwashed with brine (3×300 mL)
  4. dry with materialdried (Na2SO4)
  5. customSolvent was evaporated from the dichloromethane solution
  6. additionthe residue was treated with isopropanol (400 mL)
  7. temperaturecooled
  8. customThe pale yellow crystalline product formed
  9. filtrationwas filtered
  10. washwashed with ice-cold isopropanol
  11. customdried (168.6 g, 90%)

出典と根拠

ORDレコード
ord-86566bb997a64657a59bc5897ca9a4fb
出典データセット
uspto-grants-2002_03
特許番号
US06362182B1

関連ノート

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