Sodium Carbonate → Methanone, [1-(2-chloroethyl)-4-piperidinyl](4-fluorophenyl)-

HRID 2459

Reaction equation

HRID 2459 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:7][CH2:6]1.C(=O)([O-])[O-].[Na+].[Na+]>CCOCC>[Cl:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([C:11](=[O:19])[C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 675753381-(2-Chloroethyl)-4-(4-fluorobenzoyl)piperidine hydrochloride

Product 1

HCID 10516150Methanone, [1-(2-chloroethyl)-4-piperidinyl](4-fluorophenyl)-Yield 92.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-(2-Chloroethyl)-4-(4-fluorobenzoyl)piperidine hydrochloride (800 mg, 2.61 mmol) was suspended in ether (20 ml). With cooling in an ice bath, saturated sodium carbonate aqueous solution (5 ml) was added dropwise to the suspension. The reaction solution was extracted with ether and washed with saturated brine, and the resulting organic layer was dried on anhydrous sodium carbonate. Thereafter, the organic layer was filtered through silica gel (5 g), the solvent was removed by evaporation and then the resulting residue was purified by subjecting it to a silica gel column chromatography (ether) to obtain 650 mg (92.3%) of the title compound in the form of light yellow solid.

Workup

  1. temperatureWith cooling in an ice bath
  2. extractionThe reaction solution was extracted with ether
  3. washwashed with saturated brine
  4. dry with materialthe resulting organic layer was dried on anhydrous sodium carbonate
  5. filtrationThereafter, the organic layer was filtered through silica gel (5 g)
  6. customthe solvent was removed by evaporation
  7. customthe resulting residue was purified

Sources & evidence

ORD record
ord-0679f3c83e8041a093c3b3901f299d06
Source dataset
uspto-grants-1998_03
Patent number
US05728835

Linked notes

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