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

HRID 845616Notes

Reaction equation

HRID 845616 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 200° 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 anhydrous 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 anhydrous magnesium sulfate
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a55aebe7423442c598f51045e087b102
Source dataset
uspto-grants-1988_07
Patent number
US04758668

Reaction notes

Loading…