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

HRID 272983Notes

Reaction equation

HRID 272983 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

{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]+.

Workup

  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

Sources & evidence

ORD record
ord-bbc7a8f7c7b94b7dba9e34281812d1a4
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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