1,4-Dioxane → HCID 21273617, compound

HRID 1382847Notes

Reaction equation

HRID 1382847 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([CH2:10][CH2:11][CH2:12][C:13]3[CH:33]=[CH:32][CH:31]=[CH:30][C:14]=3[O:15][CH2:16][CH:17]([OH:29])[CH2:18][N:19]([CH2:26][CH2:27][CH3:28])[C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.O1CCOCC1.[Cl:40]N1C(=O)CCC1=O>O>[Cl:40][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:10][CH2:11][CH2:12][C:13]2[CH:33]=[CH:32][CH:31]=[CH:30][C:14]=2[O:15][CH2:16][CH:17]([OH:29])[CH2:18][N:19]([CH2:26][CH2:27][CH3:28])[C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[NH:1][CH:2]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 31398ChlorosuccinimideHCID 21273611HCID 21273611, compound

Product 1

HCID 21273617HCID 21273617, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.3 g of the product of Step A, 100 ml of dioxane and 2 g of N-chlorosuccinimide was stirred under an inert atmosphere for 19 hours at room temperature and was then diluted with water. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried and evaporated to dryness. The residue was chromatographed over silica and eluted with a 6-3-1 chloroform-cyclohexane-triethylamine mixture to obtain 4.73 g of N-[3-[2-[3-(3-chloro-1H-indol-4-yl)-propyl]-phenoxy]-2-hydroxypropyl]-N-propyl-trifluoroacetamide.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic phase was washed with water
  3. customdried
  4. customevaporated to dryness
  5. customThe residue was chromatographed over silica
  6. washeluted with a 6-3-1 chloroform-cyclohexane-triethylamine mixture

Sources & evidence

ORD record
ord-1f16f5f43eea4b9584deea9d8c8368e6
Source dataset
uspto-grants-1989_02
Patent number
US04808609

Reaction notes

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