Ethanol → HCID 70373410, compound

HRID 1709919Notes

Reaction equation

HRID 1709919 reaction equation
C[O:2]C(=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:5]=1[O:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([CH:22]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:18][CH2:17]1.[OH-:38].[K+].[CH2:40]([OH:42])C>O>[OH2:2].[F:36][C:33]1[CH:32]=[CH:31][C:30]([CH:22]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH:19]2[CH2:18][CH2:17][N:16]([CH2:15][CH2:14][CH2:13][O:12][C:5]3[CH:4]=[CH:9][C:8]([C:40]([OH:42])=[O:38])=[CH:7][C:6]=3[O:10][CH3:11])[CH2:21][CH2:20]2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 86744175HCID 86744175, compound

Product 1

HCID 70373410HCID 70373410, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-[3-[4-[bis(4-fluorophenyl)methyl]-1-piperidinyl]-propoxy-3-methoxybenzoic acid methyl ester (18.58 g, 0.0365 mole) in 400 ml of ethanol was heated for 6 hr at reflux with potassium hydroxide (16.8 g) in 50 ml of water. The ethanol was removed by rotary evaporation. Next, 1N sulfuric acid (~200 ml) was added. The aqueous phase was made neutral to litmus paper by the addition of 5% sodium hydroxide. The neutral aqueous layer was extracted several times with chloroform. The chloroform layer was dried over sodium sulfate, filtered, and solvent removed to give a white solid. The white solid was triturated with ethyl ether and cooled to about 0° C. The white solid was then collected by filtration and dried in vacuo overnight at 80° C. to give 11.38 g (61.8% yield) of white, crystalline product, the title compound, mp 123°-126° C.

Workup

  1. customThe ethanol was removed by rotary evaporation
  2. additionNext, 1N sulfuric acid (~200 ml) was added
  3. additionThe aqueous phase was made neutral to litmus paper by the addition of 5% sodium hydroxide
  4. extractionThe neutral aqueous layer was extracted several times with chloroform
  5. dry with materialThe chloroform layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customsolvent removed
  8. customto give a white solid
  9. customThe white solid was triturated with ethyl ether
  10. filtrationThe white solid was then collected by filtration
  11. customdried in vacuo overnight at 80° C.
  12. customto give 11.38 g (61.8% yield) of white, crystalline product

Sources & evidence

ORD record
ord-8ab082b61bca49c58b39b1eeb42f0d52
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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