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Potassium Carbonate → 2-nitro-N-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-Pyran-4-yl}methyl)aniline

HRID 272983
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HRID 272983 반응식
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH2:22][NH2:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.F[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N+:31]([O-:33])=[O:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[NH:23][CH2:22][C:16]1([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:11][CH:12]=2)[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1)([O-:33])=[O:32]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 11645410(4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-yl}methylamine

생성물 1

HCID 685760832-nitro-N-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-Pyran-4-yl}methyl)aniline수율 138%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

{4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-yl}methylamine (300 mg, 0.94 mmol), 2-fluoronitrobenzene (100 μl, 0.95 mmol) and potassium carbonate (150 mg, 1.08 mmol) were stirred together at room temperature in N,N-dimethylformamide (1 ml) for 2 days. The reaction mixture was concentrated in vacuo and the residue partitioned between water (30 ml) and ethyl acetate (100 ml). The layers were separated and the organic phase washed with water (2×20 ml), dried over sodium sulphate, filtered and concentrated in vacuo to give the title compound as a yellow gum (570 mg, 100%). HRMS ESI+ m/z 440.2537 [MH]+.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between water (30 ml) and ethyl acetate (100 ml)
  3. customThe layers were separated
  4. washthe organic phase washed with water (2×20 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-bbc7a8f7c7b94b7dba9e34281812d1a4
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07456164B2

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