Acetonitrile → 5-HT6/7 antagonist 1

HRID 2256576Notes

Reaction equation

HRID 2256576 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-])([O-])=O.[K+].[K+].BrCC[C:26]1[CH:36]=[CH:35][CH:34]=[C:28]2[C:29]([NH:31][C:32](=[O:33])[C:27]=12)=[O:30].[C:37](#N)[CH3:38]>>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:37][CH2:38][N:31]4[C:32](=[O:33])[C:27]5=[CH:26][CH:36]=[CH:35][CH:34]=[C:28]5[C:29]4=[O:30])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 219600212-Bromoethylphthalimide

Product 1

HCID 98653575-HT6/7 antagonist 1

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (5.15 g, 23.4 mmol), K2CO3 (4.2 g, 30.4 mmol) and 2-bromoethyl phthalimide (7.13 g, 28 mmol) in acetonitrile (250 ml) was heated at reflux for 3.5 hours. The solids and solvent were removed. The residue was purified by flash chromatography (SiO2 110 g, eluted with 2-4% CH3OH:DCM). The product thus obtained weighed 7.8 g (84%). Part of the material was recrystallized to give 2.35 g of off white crystals, m.p.=148°-149° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. customThe solids and solvent were removed
  4. customThe residue was purified by flash chromatography (SiO2 110 g, eluted with 2-4% CH3OH:DCM)
  5. customThe product thus obtained
  6. customPart of the material was recrystallized
  7. customto give 2.35 g of off white crystals, m.p.=148°-149° C.

Sources & evidence

ORD record
ord-c3730db6bd5a4e1fbeb3db8fb8ba8ca2
Source dataset
uspto-grants-1997_08
Patent number
US05654319

Reaction notes

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