Potassium Iodide → alpha-(2,3-dihydro-1,4-benzodioxin-2-yl)-4-([1H]-indol-3-yl)-1,2,3,6-tetrahydro-1-pyridine-ethanol

HRID 866655Notes

Reaction equation

HRID 866655 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH:15]=2)=[CH:2]1.Cl[CH2:17][CH:18]([C:20]1[O:25][C:24]2[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=2[O:22][CH:21]=1)[OH:19].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[O:25]1[C:24]2[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=2[O:22][CH2:21][CH:20]1[CH:18]([OH:19])[CH2:17][N:13]1[CH2:12][CH:11]=[C:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 12733300alpha-(Chloromethyl)-1,4-benzodioxin-2-methanol

Product 1

HCID 20320084alpha-(2,3-dihydro-1,4-benzodioxin-2-yl)-4-([1H]-indol-3-yl)-1,2,3,6-tetrahydro-1-pyridine-ethanolYield 26.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5 g of the product of Step A, 5.4 g of α-(chloromethyl)-1,4-benzodioxin-2-methanol, 5.5 g of sodium carbonate, 4.2 g of potassium iodide and 100 ml of dimethylformamide was heated at 100° C under nitrogen for 24 hours and was then cooled and filtered. The filtrate was poured into ice and the gum formed was extracted with methylene chloride. The organic phase was washed, dried over calcium chloride and evaporated to dryness. The brown oily residue was chromatographed over silica gel and was eluted with a 98-2 methylene chloride-methanol mixture. The combined eluates were evaporated to dryness and the residue was crystallized from isopropanol to obtain 2.5 g of α-(2,3-dihydro-1,4-benzodioxin-2-yl)-4-([1H]-indol-3-yl)-1,2,3,6-tetrahydro-1-pyridine-ethanol melting at 177° C.

Workup

  1. temperaturewas then cooled
  2. filtrationfiltered
  3. additionThe filtrate was poured into ice
  4. customthe gum formed
  5. extractionwas extracted with methylene chloride
  6. washThe organic phase was washed
  7. dry with materialdried over calcium chloride
  8. customevaporated to dryness
  9. customThe brown oily residue was chromatographed over silica gel
  10. washwas eluted with a 98-2 methylene chloride-methanol mixture
  11. customThe combined eluates were evaporated to dryness
  12. customthe residue was crystallized from isopropanol

Sources & evidence

ORD record
ord-5f117312448146b9af0cbc4d36a15d15
Source dataset
uspto-grants-1978_07
Patent number
US04100291

Reaction notes

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