Sodium Hydroxide → 3-(4-Isopropylphenyl)-1',4,6,7-tetramethylspiro[benzofuran-2(3H),4'-piperidine]-5-amine

HRID 1017868

반응식

HRID 1017868 반응식
[B-](F)(F)(F)F.[N:6]#[O+].[CH:8]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[C:21]3([CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[O:20][C:19]3[C:28]([CH3:34])=[C:29]([CH3:33])[CH:30]=[C:31]([CH3:32])[C:18]2=3)=[CH:13][CH:12]=1)([CH3:10])[CH3:9].[OH-].[Na+]>C(#N)C>[CH:8]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[C:21]3([CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]3)[O:20][C:19]3[C:28]([CH3:34])=[C:29]([CH3:33])[C:30]([NH2:6])=[C:31]([CH3:32])[C:18]2=3)=[CH:13][CH:12]=1)([CH3:10])[CH3:9]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 11137142Nitrilooxonium tetrafluoroborateHCID 219613123-(4-Isopropylphenyl)-1',4,6,7-tetramethylspiro[benzofuran-2(3H),4'-piperidine]

생성물 1

HCID 219613023-(4-Isopropylphenyl)-1',4,6,7-tetramethylspiro[benzofuran-2(3H),4'-piperidine]-5-amine수율 83%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

A solution of nitrosyl tetrafluoroborate (470.7 mg, 4.03 mmol) in acetonitrile (40 ml) was cooled to 0° C. To the solution was added a solution of 3-(4-isopropylphenyl)-1′,4,6,7-tetramethylspiro[benzofuran-2(3H),4′-piperidine] (479.1 mg, 1.32 mmol) in acetonitrile (10 ml) and the mixture was stirred for 20 minutes. The reaction mixture was poured into ice water and basified with an 8 N aqueous solution of sodium hydroxide. The product was extracted twice with ethyl acetate. The combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was dissolved into ethanol (20 ml) and palladium-carbon (59.9 mg) was added into the solution, then the mixture was stirred at 60° C. for 18 hours under a hydrogen atmosphere. The reaction mixture was cooled down to room temperature, filtered to remove insoluble materials, and then concentrated under reduced pressure. The residue was subjected to column chromatography (on Chromatorex NHDM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.); hexane-ethyl acetate 3:1) to obtain 402.0 mg (83% yield) of the title compound. Melting point: 123-124° C. (Hexane).

후처리

  1. extractionThe product was extracted twice with ethyl acetate
  2. washThe combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate
  3. customdried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved into ethanol (20 ml) and palladium-carbon (59.9 mg)
  7. additionwas added into the solution
  8. stirringthe mixture was stirred at 60° C. for 18 hours under a hydrogen atmosphere
  9. filtrationfiltered
  10. customto remove insoluble materials
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8e1a984f0ad74d55afb1daa934da34c3
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479536B1

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