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Potassium Carbonate → 1-[(5-Amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)-methyl]-N-[bis(4-fluorophenyl)methyl]-4-piperidinamine

HRID 565705
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HRID 565705 반응식
Br[CH2:2][C:3]1([CH3:16])[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[NH:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.O>[NH2:14][C:9]1[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]2[O:4][C:3]([CH2:2][N:29]3[CH2:30][CH2:31][CH:26]([NH:25][CH:24]([C:21]4[CH:20]=[CH:19][C:18]([F:17])=[CH:23][CH:22]=4)[C:32]4[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=4)[CH2:27][CH2:28]3)([CH3:16])[CH2:7][C:6]=2[C:8]=1[CH3:15]
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 108505902-Bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamineHCID 22111003N-[Bis(4-fluorophenyl)methyl]piperidin-4-amine

생성물 1

HCID 221111031-[(5-Amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)-methyl]-N-[bis(4-fluorophenyl)methyl]-4-piperidinamine수율 39%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 31374Dimethylacetamide용매

반응 조건

온도
172 °C

실험 절차

Under argon gas, a suspension of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (1.4 g), N-[bis(4-fluorophenyl)methyl]-4-piperidinamine (4.5 g), and potassium carbonate (1.4 g) in N,N-dimethylacetamide (20 mL) was stirred at 172° C. for 4.5 hours. This reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water and saturated aqueous sodium chloride solution, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatograph (silica gel/ethyl acetate and basic silica gel/hexane:ethyl acetate=9:1-85:15) and recrystallized from ethyl acetate-hexane to provide the title compound (0.97 g, yield 39%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated aqueous sodium chloride solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatograph (silica gel/ethyl acetate and basic silica gel/hexane:ethyl acetate=9:1-85:15)
  6. customrecrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-54304349fe7b45a5905c75eff1849536
출처 데이터셋
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06172085B2

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