Sodium Hydroxide → HCID 19094164, compound

HRID 487134Notes

Reaction equation

HRID 487134 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[F:32][C:29]1[CH:30]=[CH:31][C:26]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH2:14][CH2:13]2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19094136HCID 19094136, compound

Product 1

HCID 19094164HCID 19094164, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.64 g of ethyl 4-{1-[2-bis(4-fluorophenyl)methoxyethyl]-4-piperidyl}butyrate (prepared as described in Example 34) were added to 15 ml of ethanol, and then 10 ml of a 10% w/v aqueous solution of sodium hydroxide were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was then concentrated by evaporation under reduced pressure, and the resulting residue was diluted with water. The pH was then adjusted to a value of 4 by the addition of aqueous hydrochloric acid, and then the mixture was extracted with ethyl acetate. The crystals obtained from the extract were recrystallized from ethanol to afford 1.46 g (95% yield) of the title compound, melting at 145°-147° C.

Workup

  1. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  2. additionthe resulting residue was diluted with water
  3. additionThe pH was then adjusted to a value of 4 by the addition of aqueous hydrochloric acid
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe crystals obtained from the extract
  6. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-be8033c2e30c4eb788ec55fc2ee05412
Source dataset
uspto-grants-1994_03
Patent number
US05294623

Reaction notes

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