Diethyl Ether → 1-(4-Fluorobenzoyl)-3-(1-methyl-4-piperidinyl)-1H-indazole

HRID 652140Notes

Reaction equation

HRID 652140 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][N:9]=2)[CH2:4][CH2:3]1.CCOCC.[F:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1>>[F:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([CH:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)=[N:9]2)=[O:28])=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 678794-Fluorobenzoyl chlorideHCID 178480237HCID 178480237, compound

Product 1

HCID 140325191-(4-Fluorobenzoyl)-3-(1-methyl-4-piperidinyl)-1H-indazoleYield 53%

Procedure

A solution of 3.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole in 15 ml of 4-fluorobenzoyl chloride was heated at 100° for 2 hrs. The reaction mixture was poured into ether and the precipitate was collected. The precipitate was treated with dilute aqueous sodium hydroxide solution and extracted with chloroform. The chloroform extract was dried over anydrous magnesium sulfate and the solvent removed in vacuo to yield 2.5 g (53%) of product, mp 132°-133° C.

Workup

  1. customthe precipitate was collected
  2. additionThe precipitate was treated with dilute aqueous sodium hydroxide solution
  3. extractionextracted with chloroform
  4. extractionThe chloroform extract
  5. dry with materialwas dried over anydrous magnesium sulfate
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-eb4250f04dce4aada90fd2cb8a91182e
Source dataset
uspto-grants-1987_06
Patent number
US04670447

Reaction notes

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