Acetonitrile → 5-HT6/7 antagonist 1

HRID 2211535Notes

Reaction equation

HRID 2211535 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 gm, 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 gm, 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-bb33b8dc893c4d93ad40aa5a71c59b9f
Source dataset
uspto-grants-2006_09
Patent number
USRE039265E1

Reaction notes

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