Piperazine → HCID 9858707, compound

HRID 1793852Notes

Reaction equation

HRID 1793852 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1F.C(=O)([O-])[O-].[K+].[K+].[NH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1

Participants

4

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 11334553HCID 11334553, compound

Product 1

HCID 9858707HCID 9858707, compoundYield 93%

Procedure

A mixture of (5RS)-3-(3,4-difluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-4,5-dihydroisoxazole (528 mg, 2 mM), potassium carbonate (414 mg, 3 mM), and piperazine (7.5 g) was heated under nitrogen at 130° for 4 hours. After cooling, the mixture was partitioned between water (150 ml) and ethyl acetate (150 ml). The organic extract was washed with sodium bicarbonate (75 ml), and brine (75 ml). After drying (magnesium sulfate) and evaporation, the desired product (614 mg) was obtained sufficiently pure without chromatography. MS (ESP): 331 (MH+) for C16H19FN6O NMR (DMSO-d6) δ: 2.81 (t, 4H); 2.97 (t, 4H); 3.20 (dd overlapped by H2O, 1H); 3.52 (dd, 1H); 4.58 (dd, 1H); 4.64 (dd, 1H); 5.08 (m, 1H); 7.02 (t, 1H); 7.30 (overlapping m, 2H); 7.70 (d, 1H); 8.11 (d, 1H); NH missing—exchanged.

Workup

  1. temperaturewas heated under nitrogen at 130° for 4 hours
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between water (150 ml) and ethyl acetate (150 ml)
  4. extractionThe organic extract
  5. washwas washed with sodium bicarbonate (75 ml), and brine (75 ml)
  6. customAfter drying
  7. custom(magnesium sulfate) and evaporation

Sources & evidence

ORD record
ord-27972a76efd4450da10761270248a017
Source dataset
uspto-grants-2006_04
Patent number
US07022705B2

Reaction notes

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