Dimethylformamide → HCID 13019591, compound

HRID 2285722Notes

Reaction equation

HRID 2285722 reaction equation
N1C[CH:5]=[C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:16])[CH:14]=3)[NH:9][CH:8]=2)[CH2:3]C1.[CH3:17][N:18]([CH3:21])[CH:19]=O.[C:22](=[O:25])([O-])[O-].[K+].[K+]>O>[O:25]([CH2:22][CH2:17][N:18]1[CH2:21][CH:5]=[C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:16])[CH:14]=3)[NH:9][CH:8]=2)[CH2:3][CH2:19]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 30505325-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 13019591HCID 13019591, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8 g of 3-[1,2,3,6-tetrahydro-4-pyridinyl]-5-chloro-1H-indole [described in French Pat. No. 2,362,628], 80 ml of dimethylformamide, 7.5 g of potassium carbonate and 9 g of β-bromo-phenethanol was stirred at 50° C. under an inert atmosphere for 2 hours and was then cooled to room temperature and was slowly diluted with 400 ml of distilled water. The mixture was stirred for 30 minutes and was vacuum filtered. The recovered product was washed with water, then with a 1-1 water-ethanol mixture and dried to obtain 14 g of raw product. 15.8 g of the said product were chromatographed over silica gel and eluted with a 6-3-1 chloroform-acetone-triethylamine mixture. The product was crystallized from ethanol to obtain 11.53 g of 3-[1-(2-phenoxyethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-5-chloro-1H-indole melting at 172° C.

Workup

  1. filtrationfiltered
  2. washThe recovered product was washed with water
  3. dry with materialwith a 1-1 water-ethanol mixture and dried
  4. customto obtain 14 g of raw product
  5. custom15.8 g of the said product were chromatographed over silica gel
  6. washeluted with a 6-3-1 chloroform-acetone-triethylamine mixture
  7. customThe product was crystallized from ethanol

Sources & evidence

ORD record
ord-12c82b58cb7c4d89a0af9ee239f249c5
Source dataset
uspto-grants-1982_04
Patent number
US04324790

Reaction notes

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