Acetonitrile → 5-HT6/7 antagonist 1

HRID 2379973Notes

Reaction equation

HRID 2379973 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 gm 23 4 mmol) K2CO3 (4.2 gm, 30.4 mmol) and 2-bromoethyl phthalimide (7.13 gm, 28 mmol) in acetonitrile (250 ml) was heated at reflux for 3.5 hr. The solids and solvent were removed. The residue was purified by flash chromatography (SiO2, 110 m, eluted with 2-4% CH3OH:DCM). The product thus obtained weighed 7.8 gm (84%). Part of the material was recrystallized to give 2.35 gm of off white crystals, m.p.=148°-149° C.

Workup

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

Sources & evidence

ORD record
ord-e69224b136214c4f82d9473c1624bc5b
Source dataset
uspto-grants-1994_11
Patent number
US05364866

Reaction notes

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