Sodium Bicarbonate → HCID 67947350, compound

HRID 345496Notes

Reaction equation

HRID 345496 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[OH:13])[CH2:8][CH2:7]1)C.C(=O)(O)[O-].[Na+]>C(O)C.O>[OH2:3].[F:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)([OH:13])[CH:9]2[CH2:8][CH2:7][N:6]([CH2:5][C:4]([OH:28])=[O:3])[CH2:11][CH2:10]2)=[CH:19][CH:18]=1.[F:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]([CH:9]2[CH2:8][CH2:7][N:6]([CH2:5][C:4]([OH:28])=[O:3])[CH2:11][CH2:10]2)([OH:13])[C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 15042236HCID 15042236, compound

Product 1

HCID 67947350HCID 67947350, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 5.0 g (0.013 mole) of 4-[bis(4-fluorophenyl)hydroxymethyl]-1-piperidineacetic acid ethyl ester in 100 mL of 95% ethanol was added a solution of 10.9 g (0.130 mole) of sodium bicarbonate in 150 mL of water and the mixture was heated at reflux for 16 h. The solution was cooled and concentrated under reduced pressure. The residue was partitioned between ethyl ether and water (200 mL each). The layers were separated, and the aqueous layer was further extracted with two 100 mL portions of ethyl ether. The aqueous layer pH was adjusted to 6 with glacial acetic acid, whereupon a solid precipitate began to form. After standing for 16 h, the crystals were collected by filtration, washed with water and recrystallized from 2-propanol to yield 1.7 g (36%) of white solid, mp 198°-200° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 h
  3. temperatureThe solution was cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between ethyl ether and water (200 mL each)
  6. customThe layers were separated
  7. extractionthe aqueous layer was further extracted with two 100 mL portions of ethyl ether
  8. customto form
  9. filtrationthe crystals were collected by filtration
  10. washwashed with water
  11. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-150f1cf3cfc04550993d81dc4db7f689
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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