Potassium Iodide → (+/-)-8-{3-[1-(2,3-Dihydro-1H-inden-1-yl)-4-piperidinyl]propanoyl}-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one hydrochloride

HRID 2374627

반응식

HRID 2374627 반응식
[Cl:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[NH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19]([C:21]2[CH:22]=[C:23]3[C:28]4=[C:29]([CH2:31][CH2:32][N:27]4[C:26](=[O:33])[CH2:25][CH2:24]3)[CH:30]=2)=[O:20])[CH2:13][CH2:12]1.[K].[I-].[K+]>C(#N)C>[ClH:1].[CH:2]1([N:11]2[CH2:12][CH2:13][CH:14]([CH2:17][CH2:18][C:19]([C:21]3[CH:22]=[C:23]4[C:28]5=[C:29]([CH2:31][CH2:32][N:27]5[C:26](=[O:33])[CH2:25][CH2:24]4)[CH:30]=3)=[O:20])[CH2:15][CH2:16]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 944651-Chloro-2,3-dihydro-1H-indeneHCID 5462222PotassiumHCID 99665448-[3-(4-piperidinyl)propanoyl]1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

생성물 1

HCID 21888068(+/-)-8-{3-[1-(2,3-Dihydro-1H-inden-1-yl)-4-piperidinyl]propanoyl}-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one hydrochloride수율 27.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1-Chloroindane (360 mg) was added to a suspension of 8-[3-(4-piperidinyl)propanoyl]1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (700 mg), potassium carboante (700 mg) and potassium iodide (catalytic amount) in acetonitrile (10 ml) at room temperature, the mixture was stirred for 12 hours, and the reaction mixture was concentrated under reduced pressure. Water (15 ml) and ethyl acetate (20 ml) were added to the residue, and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluting solvent; ethyl acetate-methanol (9:1)) to give a free base compound of the title compound as colorless crystals (285 mg) having a melting point of 111 to 113° C. The free base compound (270 mg) was treated with a hydrogen chloride-ethanol solution to give the title compound (270 mg) as pale yellow amorphous powders.

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionWater (15 ml) and ethyl acetate (20 ml) were added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (eluting solvent; ethyl acetate-methanol (9:1))

출처 및 근거

ORD 기록
ord-c92330da27184475a4c9d29052072674
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462628B2

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