Butyl bromide → HCID 18695586, compound

HRID 1586459Notes

Reaction equation

HRID 1586459 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][CH2:21][CH3:22])[N:12]=2)=[O:10])[CH2:4][CH2:3]1.[F-].[K+].Br[CH2:26][CH2:27][CH2:28][CH3:29]>C(#N)C>[CH2:26]([N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][CH2:21][CH3:22])[N:12]=2)=[O:10])[CH2:4][CH2:3]1)[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 522689Potassium FluorideHCID 69945232HCID 69945232, compound

Product 1

HCID 18695586HCID 18695586, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of N-(4-piperidyl)-1-n-propylindazole-3-carboxamide hydrochloride (0.52 g) obtained in Example 20 in acetonitrile were successively added 50% potassium fluoride--Celite (1.10 g) and 1-bromobutane (0.22 ml), and the mixture was heated under reflux for 11 hours. The reaction solution was filtered off, distilled off under reduced pressure, and to the residue was added chloroform and saturated aqueous sodium hydrogencarbonate. After extraction with chloroform, the chloroform layer was dried over anhydrous potassium carbonate, and distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to give the title compound (0.42 g) as a yellow oily substance. Yield=69%.

Workup

  1. temperatureunder reflux for 11 hours
  2. filtrationThe reaction solution was filtered off
  3. distillationdistilled off under reduced pressure
  4. additionto the residue was added chloroform and saturated aqueous sodium hydrogencarbonate
  5. extractionAfter extraction with chloroform
  6. dry with materialthe chloroform layer was dried over anhydrous potassium carbonate
  7. distillationdistilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-79a0fb990f7d4dd18afb192911cf07b9
Source dataset
uspto-grants-1999_08
Patent number
US05945434

Reaction notes

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