Hydrochloric Acid → HCID 13589011, compound

HRID 648949Notes

Reaction equation

HRID 648949 reaction equation
Cl.O[C:3]1([C:24]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH:26]=[CH:27][NH:28]3)[CH2:8][CH2:7][N:6]([CH2:9][CH:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH:22]=[CH2:23])[OH:11])[CH2:5][CH2:4]1.Cl.C(O)C.C(=O)([O-])[O-].[K+].[K+]>O>[NH:28]1[C:29]2[C:25](=[C:24]([C:3]3[CH2:8][CH2:7][N:6]([CH2:9][CH:10]([CH2:12][O:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[O:20][CH2:21][CH:22]=[CH2:23])[OH:11])[CH2:5][CH:4]=3)[CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:27]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 11430Potassium CarbonateHCID 13589010HCID 13589010, compound

Product 1

HCID 13589011HCID 13589011, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 9.3 g of the free base of Example 10, 300 ml of lN hydrochloric acid and 100 ml of ethanol was refluxed for 3 hours and the mixture was diluted with water and made alkaline. The aqueous phase was saturated with potassium carbonate and was extracted with ethyl acetate. The organic phase was chromatographed over silica gel and eluted with a 6-3-1 cyclohexane-chloroform-triethylamine mixture to obtain 7.7 g of 4-(1H-indole-4-yl)-α-[[2-(2-propenyloxy)-phenoxy]-methyl]-1,2,3,6-tetrahydro-1-pyridine ethanol with an Rf=0.05.

Workup

  1. extractionwas extracted with ethyl acetate
  2. customThe organic phase was chromatographed over silica gel
  3. washeluted with a 6-3-1 cyclohexane-chloroform-triethylamine mixture

Sources & evidence

ORD record
ord-bf722432cea642d0858a134c577064d4
Source dataset
uspto-grants-1988_04
Patent number
US04737505

Reaction notes

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