Acetic Acid → HCID 86744172, compound

HRID 1709882Notes

Reaction equation

HRID 1709882 reaction equation
C([O:3][C:4](=[O:37])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([C:21](C3C=CC(F)=CC=3)([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)O)[CH2:17][CH2:16]2)=[CH:7][CH:6]=1)C.[OH-:38].[K+].[C:40](O)(=O)[CH3:41].[Cl-:44].[Na+]>C(O)C.O>[OH2:3].[ClH:44].[F:29][C:26]1[CH:27]=[CH:28][C:23]([CH:21]2[CH2:18][CH2:19][CH2:20][N:15]([CH2:14][CH2:13][CH2:12][O:11][C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:3])=[O:37])=[CH:6][CH:7]=3)[C:16]2([C:41]2[CH:40]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:17][OH:38])=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 14407102HCID 14407102, compound

Product 1

HCID 86744172HCID 86744172, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2.7 g (0.005 mole) of 4-[3-[4-[bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]propoxy]benzoic acid ethyl ester and 1.2 g(0.022 mole) of potassium hydroxide in 50 ml of ethanol and 20 ml of water was heated on a steam bath for 2 hr. Acetic acid, 10 ml, was added and the solution was poured into 500 ml of ice water and the mixture was allowed to stand at ambient temperature overnight. Sodium chloride was added to the mixture to give a coagulated solid. The solid was collected by filtration and air dried. The solid was dissolved in 20 ml of isopropyl alcohol and the solution was poured into 30 ml of ethereal hydrogen chloride. The salt which gradually crystallized was collected by filtration, washed with ethyl ether and dried to give 0.2 g (8%) of white powder, m.p. 148°-158° C. with decomposition.

Workup

  1. customto give a coagulated solid
  2. filtrationThe solid was collected by filtration and air
  3. customdried
  4. dissolutionThe solid was dissolved in 20 ml of isopropyl alcohol
  5. additionthe solution was poured into 30 ml of ethereal hydrogen chloride
  6. customThe salt which gradually crystallized
  7. filtrationwas collected by filtration
  8. washwashed with ethyl ether
  9. customdried

Sources & evidence

ORD record
ord-6426e8772f7345c29d213b5bb0cb21de
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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