1,4-Dibromobutane → 4-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]butylbromide

HRID 1069319Notes

Reaction equation

HRID 1069319 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+].[Br:23][CH2:24][CH2:25][CH2:26][CH2:27]Br>C(#N)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:27][CH2:26][CH2:25][CH2:24][Br:23])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 219601214-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]butylbromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (12 g, 55 mmol), K2CO3 (13 g) and 1,4dibromobutane (20 g, 9.3 mmol, 1.7 eq) in acetonitrile (300 ml) was stirred at room temperature overnight. The inorganic material was filtered. The solution was concentrated to ˜80 ml, when crystals crashed out. The product was filtered to yield 14.16 g (73%), m.p.=243-245° C.

Workup

  1. filtrationThe inorganic material was filtered
  2. concentrationThe solution was concentrated to ˜80 ml, when crystals
  3. filtrationThe product was filtered
  4. customto yield 14.16 g (73%), m.p.=243-245° C.

Sources & evidence

ORD record
ord-5194b59f5d23438097699af73d5d7145
Source dataset
uspto-grants-2001_06
Patent number
US06251907B1

Reaction notes

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