Benzoyl chloride → HCID 14032556, compound

HRID 1722134Notes

Reaction equation

HRID 1722134 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31]>CCOCC>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[C:18]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=2)[C:6]([CH:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[N:7]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 444972Fumaric AcidHCID 178480245HCID 178480245, compound

Product 1

HCID 14032556HCID 14032556, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of 3.1 g of 6-fluoro-3-(1-methyl-4-piperidinyl)-1H-indazole and 8 ml of benzoyl chloride was heated at 100° C. in a steam bath for 8 hrs. After cooling, ether was added and the solid was collected. The solid was treated with ammonium hydroxide solution to give an oil. The oil was dissolved in 300 ml of ether, stirred and 1.2 g of fumaric acid was added. After four hrs at ambient temperature, the fumarate salt was collected. Recrystallization from ethanol-ether yielded 3.0 g (50.9%) of product, mp 180°-182° C.

Workup

  1. temperatureAfter cooling
  2. customthe solid was collected
  3. additionThe solid was treated with ammonium hydroxide solution
  4. customto give an oil
  5. customthe fumarate salt was collected
  6. customRecrystallization from ethanol-ether

Sources & evidence

ORD record
ord-71d4d4de8f8344fd9bb360bf86da4c9b
Source dataset
uspto-grants-1989_08
Patent number
US04853470

Reaction notes

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