Sodium Carbonate → HCID 13019592, compound

HRID 2285723Notes

Reaction equation

HRID 2285723 reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:23][CH2:24][O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27]1>CC(CC(C)C)=O>[O:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH:26]1[O:25][CH2:24][CH2:23][N:1]1[CH2:2][CH:3]=[C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2549512-(2-Chloroethoxy)tetrahydro-2H-pyranHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 13019592HCID 13019592, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A solution of 6.93 g of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole [described in French Pat. No. 2,362,628] dissolved at 100° C. in 70 ml of isobutyl methyl ketone admixed with 11.13 g of sodium carbonate and 14 ml of 2-(2-chloroethoxy)-tetrahydro-2H-pyran was refluxed with stirring under an inert atmosphere for 51/2 hours and was then cooled and poured into ice water. The mixture was extracted with ethyl acetate and the organic phase was washed with water, with aqueous sodium chloride solution, dried and evaporated to dryness. The 9.9 g of crystalline residue was chromatographed over silica gel and eluted with an 85-10-5 chloroform-acetonetriethylamine mixture to obtain 7.85 g of 3-[1-(2-{2-tetrahydropyranyloxy}-ethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole in the form of crystals melting at 135° C.

Workup

  1. temperaturewas refluxed
  2. temperaturewas then cooled
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic phase was washed with water, with aqueous sodium chloride solution
  5. customdried
  6. customevaporated to dryness
  7. customThe 9.9 g of crystalline residue was chromatographed over silica gel
  8. washeluted with an 85-10-5 chloroform-acetonetriethylamine mixture

Sources & evidence

ORD record
ord-10d92d6d098e4db39057286d5ad7c843
Source dataset
uspto-grants-1982_04
Patent number
US04324790

Reaction notes

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