Potassium Carbonate → 1-(4-Fluorophenyl)-4-[4-(2-amino-3-nitro-pyridin-6-yl)-1-piperazinyl]-1-butanone ethylene ketal

HRID 1285134Notes

Reaction equation

HRID 1285134 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([CH2:24][CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[O:23][CH2:22][CH2:21][O:20]2)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CC>[CH2:21]1[O:20][C:19]([C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)([CH2:24][CH2:25][CH2:26][N:27]2[CH2:28][CH2:29][N:30]([C:4]3[N:3]=[C:2]([NH2:1])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=3)[CH2:31][CH2:32]2)[O:23][CH2:22]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 27831211-(3-(2-(4-Fluorophenyl)-1,3-dioxolan-2-yl)propyl)piperazine

Product 1

HCID 571457721-(4-Fluorophenyl)-4-[4-(2-amino-3-nitro-pyridin-6-yl)-1-piperazinyl]-1-butanone ethylene ketal

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

5.6 g 2-amino-6-chloro-3-nitropyridine, 10 g 1-(3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-propyl)piperazine, 5 g potassium carbonate and 100 ml n-propanol are refluxed 21/2 hours. After cooling the precipitate is filtered off. The filtrate is concentrated to ca. 10 ml and diluted with the same volume of diisopropyl ether. The resulting cristallisate is admixed with the above mentioned precipitate and partitioned between water and methylene chloride. The organic phase is filtered and evaporated to give the heading compound, m.p. 117°-118°.

Workup

  1. temperatureAfter cooling the precipitate
  2. filtrationis filtered off
  3. concentrationThe filtrate is concentrated to ca. 10 ml
  4. additiondiluted with the same volume of diisopropyl ether
  5. custompartitioned between water and methylene chloride
  6. filtrationThe organic phase is filtered
  7. customevaporated
  8. customto give the heading compound, m.p. 117°-118°

Sources & evidence

ORD record
ord-c37eaf3eae08407a8b0553640c833c89
Source dataset
uspto-grants-1986_01
Patent number
US04565816

Reaction notes

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