Ammonia → 5-(Piperazin-1-yl)benzofuran-2-carboxamide

HRID 628796

Reaction equation

HRID 628796 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13]([C:15](OC)=[O:16])=[CH:12][C:11]=3[CH:19]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[NH3:20].Cl>O>[N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13]([C:15]([NH2:20])=[O:16])=[CH:12][C:11]=3[CH:19]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 77231352Methyl 5-(piperazin-1-yl)benzofuran-2-carboxylate

Product 1

HCID 98347195-(Piperazin-1-yl)benzofuran-2-carboxamideYield 73.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 5-(1-piperazinyl)benzofuran-2-carboxylate (37 g) was added to saturated methanolic ammonia solution (1850 ml) at 25-30° C., the mixture was stirred for 6 to 16 hours at the same temperature. The reaction mass was distilled under vacuum to remove the solvent after completion of the reaction. Water (148 ml) was added to the resulting residue, followed by adjusting the pH to 2-4 with concentrated HCl and then filtering the aqueous layer. The pH of the resulting aqueous layer was adjusted to 9-10 with ammonium hydroxide solution. The separated solid was filtered, washed with water (100 ml) and then dried to produce 25.5 g of 5-(1-piperazinyl)benzofuran-2-carboxamide (Purity by HPLC: 99%; Yield: 73.1%).

Workup

  1. distillationThe reaction mass was distilled under vacuum
  2. customto remove the solvent
  3. customafter completion of the reaction
  4. filtrationfiltering the aqueous layer
  5. filtrationThe separated solid was filtered
  6. washwashed with water (100 ml)
  7. customdried

Sources & evidence

ORD record
ord-6cf50d02d20e40c0b6bc0d3da7cd02ad
Source dataset
uspto-grants-2016_04
Patent number
US09315456B2

Linked notes

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