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

HRID 1459967Notes

Reaction equation

HRID 1459967 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-1839343a6bee46a193be0b86efa6074c
Source dataset
uspto-grants-1998_12
Patent number
US05854263

Reaction notes

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