3-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole → HCID 17943138, compound

HRID 1780176Notes

Reaction equation

HRID 1780176 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1>C(O)(C)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:5][CH:4]([OH:8])[CH2:3][CH3:2])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 17943138HCID 17943138, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A stirred mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (5.5 g, 25 mmol) and 1,2-expoxybutane (1.89 g, 26.3 mmol) in isopropyl alcohol (100 ml) was heated at 65 C. for 2 days. This mixture was cooled and the solvent was removed to leave a brown oil which was purified by flash chromatography over a silica gel column (SiO2, 70 g; eluted with DCM, 1 l and MeOH:DCM 2%: 98%) to give an off-white solid weighing 6.3 g. Recrystallization from hot ethanol yielded 1.96 g of fine crystals, m.p.=87°-88° C.

Workup

  1. temperaturewas heated at 65 C
  2. temperatureThis mixture was cooled
  3. customthe solvent was removed
  4. customto leave a brown oil which
  5. customwas purified by flash chromatography over a silica gel column (SiO2, 70 g; eluted with DCM, 1 l and MeOH:DCM 2%: 98%)
  6. customto give an off-white solid
  7. customRecrystallization from hot ethanol

Sources & evidence

ORD record
ord-ce713e4e15a447e6b8c28d0af7610df3
Source dataset
uspto-grants-1997_05
Patent number
US05629326

Reaction notes

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