Potassium Carbonate → HCID 67179276, compound

HRID 241595Notes

Reaction equation

HRID 241595 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][Cl:6].[F:7][C:8]1[CH:22]=[CH:21][C:11]2[C:12]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[N:13][O:14][C:10]=2[CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:6][CH2:5][CH2:4][CH2:3][CH2:2][N:18]1[CH2:17][CH2:16][CH:15]([C:12]2[C:11]3[CH:21]=[CH:22][C:8]([F:7])=[CH:9][C:10]=3[O:14][N:13]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 67179276HCID 67179276, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-bromo-4-chlorobutane (9.4 g, 60 mmol) is dissolved in 50 ml of DMF, and thereto 4-(6-fluoro-1,2-benzisoxazolyl)-piperidine (4.4 g, 20 mmol) and anhydrous potassium carbonate powder (8.2 g, 60 mmol) is added. The mixture is stirred at room temperature for 48 hours and the reaction is terminated. To the reaction solution is added 100 ml of water and 100 ml of ethyl acetate. The mixture is shaked and the aqueous layer is further extracted with 100 ml of ethyl acetate. The ethyl acetate layers are combined, backwashed with 200 ml of water, dried over anhydrous magnesium sulfate and filtered. The filtrate is concentrated to 50 ml volume and extracted with 5% HCl (30 ml×3). The extracting solution is combined, adjusted to pH 7 with 5% NaOH, and further extracted with ethyl acetate (30 ml×3). The extracting solution is combined, dried and evaporated to dryness to obtain 1.8 g of 3-(1-(4-chlorobutyl)-4-piperidinyl)-6-fluoro-benzisoxazole, with a yield of 30%.

Workup

  1. customthe reaction is terminated
  2. additionTo the reaction solution is added 100 ml of water and 100 ml of ethyl acetate
  3. extractionthe aqueous layer is further extracted with 100 ml of ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated to 50 ml volume
  7. extractionextracted with 5% HCl (30 ml×3)
  8. extractionfurther extracted with ethyl acetate (30 ml×3)
  9. customdried
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-c1aa3701a0974a29be329ddeff2cf8fb
Source dataset
uspto-grants-2014_02
Patent number
US08653069B2

Reaction notes

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