Ethanol → HCID 68815794, compound

HRID 734299Notes

Reaction equation

HRID 734299 reaction equation
C1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)CCN1.O.O.[Na+].[Na+].[CH2:15]([N:26]([CH2:31][C:32](O)=O)[CH2:27][C:28](O)=O)[CH2:16][N:17]([CH2:22][C:23]([O-])=O)CC([O-])=O.[OH-].[NH4+].ClCCl.[CH3:40]O.C(N([CH2:47][CH3:48])CC)C.[CH2:49](O)[CH3:50]>O>[CH2:5]1[CH2:6][CH2:7][CH2:8][CH:9]2[C:10]1=[C:15]1[N:26]([CH2:27][CH2:28]2)[CH2:31][CH2:32][C:40]2[C:49]3[CH:50]=[CH:47][CH:48]=[CH:23][C:22]=3[NH:17][C:16]1=2

Participants

7

Reactant 5

HCID 702EthanolHCID 14923Ammonium HydroxideHCID 97812DecahydroisoquinolineHCID 21913430dichloromethane MeOH Et3NHCID 44120005Edta disodium

Product 1

HCID 68815794HCID 68815794, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.356 g (1.26 mmol) of N-[2-(3-indolyl)ethyl)]decahydroiso-quinoline in 20 ml of ethanol was added a solution of 1.6 g of mercuric acetate and 1.88 g of ethylenediaminetetra-acetic acid disodium salt dihydrate in 40 ml of water and the resulting mixture was refluxed for 3 h. The cooled mixture was made basic with dilute ammoniumhydroxide (pH 11) and then extracted with dichloromethane (3×30 ml). The combined organic layers were dried over sodium sulfate, filtered and the solvent evaporated to give the crude enamine (mixture of regioisomers), which was directly used in the next step (see example 36). The pure enamine could be obtained by column chromatography (silica gel, dichloromethane/methanol/triethylamine, 98:1:1).

Workup

  1. temperaturethe resulting mixture was refluxed for 3 h
  2. extractionextracted with dichloromethane (3×30 ml)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customto give the crude enamine (mixture of regioisomers), which

Sources & evidence

ORD record
ord-2a170e72a6ef41af86aa33618f992787
Source dataset
uspto-grants-2009_09
Patent number
US07592350B2

Reaction notes

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