Hydrochloric Acid → HCID 13589002, compound

HRID 648948Notes

Reaction equation

HRID 648948 reaction equation
C(O)(=O)/C=C/C(O)=O.[NH:9]1[C:17]2[C:12](=[C:13]([C:18]3(O)[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10]1.Cl.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:24][N:21]1[CH2:20][CH:19]=[C:18]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:12]=2[CH:11]=[CH:10][NH:9]3)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 13589001HCID 13589001, compound

Product 1

HCID 13589002HCID 13589002, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.4 g of the free base of Example 4 and 200 ml of lN hydrochloric acid was refluxed for 90 minutes and was then cooled to room temperature and was diluted with water. The mixture was made alkaline by addition of potassium carbonate and was then extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The 5.7 g of residue were chromatographed over silica gel and eluted with a 6-3-1 cyclohexane-chloroform-ethyl acetate mixture to obtain 2.5 g of 4-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole melting at 164° C.

Workup

  1. temperaturewas refluxed for 90 minutes
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. customdried
  5. customevaporated to dryness under reduced pressure
  6. customThe 5.7 g of residue were chromatographed over silica gel
  7. washeluted with a 6-3-1 cyclohexane-chloroform-ethyl acetate mixture

Sources & evidence

ORD record
ord-6d03979b0da34e3c958be31bbe5bddeb
Source dataset
uspto-grants-1988_04
Patent number
US04737505

Reaction notes

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