Dimethylformamide → HCID 66711099, compound

HRID 1262394Notes

Reaction equation

HRID 1262394 reaction equation
C(O[C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[C:25]([O:32][CH3:33])[CH:24]=3)[CH2:18]2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C(OC(N1C[CH2:48][N:47]([CH:50]2[CH2:55][CH2:54][CH2:53][NH:52][CH2:51]2)CC1)=O)C1C=CC=CC=1.FC(F)(F)C(O)=O.[C:63](=[O:66])([O-])[O-].[K+].[K+].F[C:70]1[CH:75]=[CH:74][C:73]([N+]([O-])=O)=[C:72](OC)[CH:71]=1.C[N:82](C=O)C>>[CH3:33][O:32][C:25]1[CH:24]=[C:23]([N:19]2[CH2:20][CH2:21][CH2:22][CH:17]([N:14]3[CH2:15][CH2:16][N:11]([CH3:9])[CH2:12][CH2:13]3)[CH2:18]2)[CH:28]=[CH:27][C:26]=1[NH:29][C:53]1[N:52]=[CH:51][C:50]2=[CH:55][CH:54]=[C:48]([C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][C:71]=3[O:66][CH3:63])[N:47]2[N:82]=1

Participants

7

Reactant 6

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 27792505-Fluoro-2-nitroanisoleHCID 66710995HCID 66710995, compoundHCID 66711201HCID 66711201, compound

Product 1

HCID 66711099HCID 66711099, compound

Conditions

Temperature
60 °C

Procedure

4-[1-(3-Methoxy-4-nitro-phenyl)-piperidin-3-yl]-piperazine-1-carboxylic acid benzyl ester: To a mixture of 4-piperidin-3-yl-piperazine-1-carboxylic acid benzyl ester, compound with trifluoro-acetic acid (10.0 g, 24.0 mmol) and potassium carbonate (8.3 g, 6.0 mmol) in DMF (100 mL) was added 4-fluoro-2-methoxy-1-nitro-benzene (4.1 g, 24 mmol) with stirring. The mixture was heated at 60° C. for 18 hours. The solvent was removed on the rotovap and the residue was partitioned between dichloromethane and water, the organic phase was washed with sat'd aq. sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. Flash chromatography over silica gel provided 9.2 g of the title compound. MS=455 (M+1).

Workup

  1. customThe solvent was removed on the rotovap
  2. customthe residue was partitioned between dichloromethane and water
  3. washthe organic phase was washed with sat'd aq. sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2aba6a566e474b30ba5a4812a21ebd9a
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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