Water → HCID 68777853, compound

HRID 2263000Notes

Reaction equation

HRID 2263000 reaction equation
FC(F)(F)C(O)=O.[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([NH:17][C:18]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:19])=[N:9]1.C(N(CC)CC)C.[CH2:33]([N:40]=[C:41]=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O>O1CCCC1>[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([NH:17][C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:41]([NH:40][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:42])[CH2:22][CH2:21]2)=[O:19])=[N:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76639Benzyl isocyanateHCID 68778018N-1,2-Benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetate

Product 1

HCID 68777853HCID 68777853, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-1,2-benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetate (200 mg, 0.555 mmol) and triethylamine (0.309 ml, 2.22 mmol) in tetrahydrofuran (4 ml) was added benzyl isocyanate (0.103 ml, 0.833 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured to water and extracted with ethyl acetate. The extract was washed with water, and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of tetrahydrofuran and ethyl acetate to give 157 mg (74.8%) of the desired product as a solid.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from a mixed solvent of tetrahydrofuran and ethyl acetate

Sources & evidence

ORD record
ord-2b97c83ca5b442d0a7a92d9bac4925ba
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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