Potassium Hydroxide → HCID 10198280, compound

HRID 2304612Notes

Reaction equation

HRID 2304612 reaction equation
C([N:6]1[CH2:11][CH:10]=[C:9]([C:12]2[C:17]3[S:18][CH:19]=[CH:20][C:16]=3[CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(OCC)=O.[OH-].[K+]>C(O)CO.O>[S:18]1[CH:19]=[CH:20][C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:9]3[CH2:10][CH2:11][NH:6][CH2:7][CH:8]=3)[C:17]1=2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 9925947HCID 9925947, compound

Product 1

HCID 10198280HCID 10198280, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent2×

Procedure

Dissolve N-carbethoxy-4-(benzo[b]thiophene-7-yl)-1,2,3,6-tetrahydropyridine (105 mg, 0.3652mmol) in 1 mL ethylene glycol and add potassium hydroxide (102 mg, 1.826 mmol) dissolved in 1 mL of water. The reaction mixture is heated at reflux for 8 hours and then cooled to room temperature. It is then diluted with 5 mL water and extracted with ethyl acetate (3×5 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The reside is purified over silica gel to provide the title compound as a yellow oil (51 mg), MS(ion spray)=216.3 (M+1).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 8 hours
  3. extractionextracted with ethyl acetate (3×5 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe reside is purified over silica gel

Sources & evidence

ORD record
ord-f1ce87c70b394ba58e9fc79025ee8ee0
Source dataset
uspto-grants-2002_08
Patent number
US06436964B1

Reaction notes

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