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

HRID 1900418Notes

Reaction equation

HRID 1900418 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 1,4-dibromobutane (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-956319b8e8484164a659d238d5cdf168
Source dataset
uspto-grants-1996_11
Patent number
US05574032

Reaction notes

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