Potassium Hydroxide → HCID 22502890, compound

HRID 1251174Notes

Reaction equation

HRID 1251174 reaction equation
CC(C)(O)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]3[CH:17]=[C:18]([N:20]4[CH2:25][CH2:24][N:23]([CH2:26][CH3:27])[CH2:22][CH2:21]4)[S:19][C:13]=3[CH:12]=2)=[CH:7][CH:6]=1.[OH-].[K+]>C(O)CCC>[C:4]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]3[CH:17]=[C:18]([N:20]4[CH2:25][CH2:24][N:23]([CH2:26][CH3:27])[CH2:22][CH2:21]4)[S:19][C:13]=3[CH:12]=2)=[CH:7][CH:6]=1)#[CH:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22503042HCID 22503042, compound

Product 1

HCID 22502890HCID 22502890, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

6-[4-(3,3-Dimethyl-3-hydroxy-1-propynyl)phenyl]-(4-ethylpiperazin-1-yl)thieno[3,2-c]pyridine (0.80 g) was dissolved in 1-butanol (15 ml), followed by the addition of potassium hydroxide (0.47 g), and the mixture was heated under reflux for 20 min. The reaction solution was evaporated, and the resulting residue was partitioned between ethyl acetate and water, and then extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was removed, and the resulting residue was dissolved in ether, and then filtered through NH-silica gel. The resulting filtrate was concentrated, to give 0.59 g of the title compound as a pale yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 min
  3. customThe reaction solution was evaporated
  4. customthe resulting residue was partitioned between ethyl acetate and water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed
  9. dissolutionthe resulting residue was dissolved in ether
  10. filtrationfiltered through NH-silica gel
  11. concentrationThe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-845f468cd8ea4a63ad9b08233e828178
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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