Hydroxide → HCID 21347708, compound

HRID 2186345Notes

Reaction equation

HRID 2186345 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH2:13][CH2:14][CH2:15][C@@H:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)[CH2:18][C@@H:17]1[C:30]([O:32]C)=[O:31].[OH-]>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH2:13][CH2:14][CH2:15][C@@H:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)[CH2:18][C@@H:17]1[C:30]([OH:32])=[O:31]

Participants

5

Reactant 2

HCID 961HydroxideHCID 86758148HCID 86758148, compound

Product 1

HCID 21347708HCID 21347708, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 0.37 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)propyl]piperidine-3-carboxylate in 6 cm3 of dioxane, to which dioxane had been added 1.6 cm3 of N aqueous hydroxide, was stirred at a temperature in the region of 60° C. for 20 hours. After evaporating the solvents under reduced pressure (5 kPa) at a temperature in the region of 45° C., the residue obtained was taken up in 20 cm3 of water and then the aqueous phase was washed with 20 cm3 of ethyl ether. After separating the ether by settling, the aqueous phase was neutralized with 1.6 cm3 of N hydrochloric acid and then extracted with 2 times 30 cm3 of ethyl acetate. The combined extracts were dried over magnesium sulfate. The organic solution, after filtration, was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 0.21 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1 -[3-(thien-2- yl)propyl]piperidine-3-carboxylic acid was obtained in the form of a foam with a beige color which melts at approximately 60° C. with softening.

Workup

  1. customAfter evaporating the solvents under reduced pressure (5 kPa) at a temperature in the region of 45° C.
  2. customthe residue obtained
  3. washthe aqueous phase was washed with 20 cm3 of ethyl ether
  4. customAfter separating the ether
  5. extractionextracted with 2 times 30 cm3 of ethyl acetate
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. filtrationThe organic solution, after filtration
  8. customwas evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-676c92d3df0b4763833afc5f94618e62
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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