1,4-Dioxane → HCID 20468250, compound

HRID 1903133Notes

Reaction equation

HRID 1903133 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)[CH2:6]1)=[O:4].O1CCOCC1.[Cl:28]N1C(=O)CCC1=O>O>[Cl:28][C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[CH:19][C:11]=2[CH:7]2[CH2:8][CH2:9][CH2:10][N:5]([C:3](=[O:4])[C:2]([F:1])([F:20])[F:21])[CH2:6]2)[NH:15][CH:14]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 31398ChlorosuccinimideHCID 20468247HCID 20468247, compound

Product 1

HCID 20468250HCID 20468250, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 10 g of the product of Step A, 300 ml of dioxane and 5 g of N-chlorosuccinimide was stirred at 20° C. for 20 hours and was then diluted with water. The mixture was extracted with ethyl acetate and the organic phase was washed with water and aqueous sodium chloride solution, was dried and evaporated to dryness. The residue was chromatographed over silica gel and was eluted with a 6-3-1 cyclohexane-chloroform-triethylamine mixture to obtain 11 g of 3-chloro-4-(1-trifluoroacetyl-piperidin-3-yl)-1H-indole which was used as is for the next step.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic phase was washed with water and aqueous sodium chloride solution
  3. customwas dried
  4. customevaporated to dryness
  5. customThe residue was chromatographed over silica gel
  6. washwas eluted with a 6-3-1 cyclohexane-chloroform-triethylamine mixture

Sources & evidence

ORD record
ord-0a348002e3c34217b41975a878454d9b
Source dataset
uspto-grants-1984_03
Patent number
US04435408

Reaction notes

Loading…