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

HRID 278907

반응식

HRID 278907 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
105 °C

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-1ea95706b739462584a9e494404570de
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362182B1

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