Acetic Acid → HCID 70373256, compound

HRID 1709933Notes

Reaction equation

HRID 1709933 reaction equation
C(O)(=O)C(O)=[O:3].C([O:9][C:10](=[O:44])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH:25]([C:28]([C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[OH:29])[CH2:24][CH2:23]2)=[CH:14][CH:13]=1)C.[OH-].[K+].O.C(O)(=O)C>C(O)C>[OH2:3].[F:43][C:40]1[CH:39]=[CH:38][C:37]([C:28]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)([OH:29])[CH:25]2[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][CH2:19][O:18][C:15]3[CH:16]=[CH:17][C:12]([CH2:11][C:10]([OH:44])=[O:9])=[CH:13][CH:14]=3)[CH2:23][CH2:24]2)=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 70373282HCID 70373282, compound

Product 1

HCID 70373256HCID 70373256, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.7 g (0.0073 mole) of the free base of 4-[3-[4-[bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]propoxy]benzeneacetic acid ethyl ester oxalate [1:1], 0.8 g (0.0145 mole) of potassium hydroxide, 10 ml of water and 50 ml of 95% ethanol was heated at reflux under a nitrogen atmosphere for 1.5 hr. The solution was poured into a mixture of 1.3 g (0.022 mole) of glacial acetic acid in 500 ml of ice water and let stand at ambient temperature overnight. The solid which had precipitated was collected by filtration, washed with water, air dried, and recrystallized from 2-propanol to yield 2.9 g (78%) of the title compound as a white solid, mp 113°-121° C. (dec).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 1.5 hr
  3. customThe solid which had precipitated
  4. filtrationwas collected by filtration
  5. washwashed with water, air
  6. customdried
  7. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-e76990b9dd5a40fd83ddcad7d0b2688a
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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