Sodium Bicarbonate → HCID 19989935, compound

HRID 345484Notes

Reaction equation

HRID 345484 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[OH:16])[CH2:11][CH2:10]1)C.C(=O)(O)[O-].[Na+]>C(O)C.O>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:15]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)([OH:16])[CH:12]2[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:31])=[O:3])[CH2:14][CH2:13]2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 150422384-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinepentanoic acid ethyl ester

Product 1

HCID 19989935HCID 19989935, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 9.0 g (0.020 mole) of 4-[bis(4-fluorophenyl)hydroxymethyl]-1-piperidinepentanoic acid ethyl ester in 300 ml of 95% ethanol was added a solution of 21.0 g (0.250 mole) of sodium bicarbonate in 250 ml of water, and the mixture was heated at reflux for 6 h under a nitrogen atmosphere. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl ether and water (300 ml each). The layers were separated, and the aqueous layer was further extracted with three 300 ml portions of ethyl ether. The aqueous layer pH was adjusted to 6 with glacial acetic acid, whereupon a soid precipitate began to form. After standing for 16 h the crystals were collected by filtration, washed with water and recrystallized from benzene to yield 4.2 g (52%) of the title compound as a white solid, mp 105°-107° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 6 h under a nitrogen atmosphere
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was partitioned between ethyl ether and water (300 ml each)
  5. customThe layers were separated
  6. extractionthe aqueous layer was further extracted with three 300 ml portions of ethyl ether
  7. customto form
  8. filtrationthe crystals were collected by filtration
  9. washwashed with water
  10. customrecrystallized from benzene

Sources & evidence

ORD record
ord-83f928db7ad247c89ade2cb08ce6b5c1
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

Loading…