Hydrochloric Acid → HCID 70437004, compound

HRID 255662Notes

Reaction equation

HRID 255662 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[N:8]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:19]=3[CH3:25])[CH:9]=[C:10]([C:15](=[O:17])[CH:16]=2)[C:11]([O:13]C)=[O:12])[CH2:3][CH2:2]1.[CH:26](Br)([CH3:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+].[ClH:36]>CN(C)C=O>[ClH:36].[OH:24][C:21]1[CH:22]=[CH:23][C:18]([N:8]2[C:7]([CH:4]3[CH2:5][CH2:6][N:1]([CH:26]([CH3:28])[CH3:27])[CH2:2][CH2:3]3)=[CH:16][C:15](=[O:17])[C:10]([C:11]([OH:13])=[O:12])=[CH:9]2)=[C:19]([CH3:25])[CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 14010737HCID 14010737, compound

Product 1

HCID 70437004HCID 70437004, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 4 ml of N,N-dimethylformamide was dissolved 0.24 g of methyl 6-(4-piperidinyl)-1-(4-hydroxy-2-methylphenyl)-4-oxo-1,4-dihydronicotinate, and 0.17 g of isopropyl bromide and 0.06 g of potassium carbonate were added to the solution, after which they were reacted at 60° C. for 6 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue was dissolved in a mixture of 20 ml of chloroform and 20 ml of water. The organic layer was separated, washed twice with 20-ml portions of water, and dried with anhydrous sodium sulfate. Then, the solvent was removed by distillation under reduced pressure, and the oily substance thus obtained was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/ethanol (20:1 by volume) mixture). The fraction containing the objective substance was concentrated, and to the oily substance thus obtained was added 5 ml of 6N hydrochloric acid, and they were refluxed for 2 hours. The solvent was removed by distillation under reduced pressure to obtain 0.11 g of 1-(4-hydroxy-2-methylphenyl)-6-(1-isopropyl-4-piperidinyl)-4-oxo-1,4-dihydronicotinic acid hydrochloride having a melting point of 195.5°-200.5° C.

Workup

  1. additionwere added to the solution
  2. customafter which they were reacted at 60° C. for 6 hours
  3. customAfter completion of the reaction
  4. customthe solvent was removed by distillation under reduced pressure
  5. dissolutionthe residue was dissolved in a mixture of 20 ml of chloroform and 20 ml of water
  6. customThe organic layer was separated
  7. washwashed twice with 20-ml portions of water
  8. dry with materialdried with anhydrous sodium sulfate
  9. customThen, the solvent was removed by distillation under reduced pressure
  10. customthe oily substance thus obtained
  11. customwas purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/ethanol (20:1 by volume) mixture)
  12. additionThe fraction containing the objective substance
  13. concentrationwas concentrated
  14. customto the oily substance thus obtained
  15. temperaturewere refluxed for 2 hours
  16. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1d4b41e82cb8457bad3f3f3620c923cd
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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