2-Chloro-4'-fluoroacetophenone → HCID 15816464, compound

HRID 1440794Notes

Reaction equation

HRID 1440794 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=2)=[O:8])[CH2:3][CH2:2]1.Cl[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)=[O:22].C(=O)(O)[O-].[Na+]>O.O1CCCC1.[Cl-].[Na+].O>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:21](=[O:22])[CH2:20][N:1]2[CH2:2][CH2:3][CH:4]([C:7]([C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:13][CH:14]=3)=[O:8])[CH2:5][CH2:6]2)=[CH:24][CH:25]=1

Participants

7

Reactant 3

HCID 1202482-Chloro-4'-fluoroacetophenoneHCID 516892Sodium BicarbonateHCID 15680074N-[4-(Piperidine-4-carbonyl)phenyl]acetamide

Product 1

HCID 15816464HCID 15816464, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3.0 g (12.2 mmol) of N-[4-(4-piperidinyl-carbonyl)phenyl]-acetamide in 10 ml of water and 100 ml of tetrahydrofuran was added 2.3 g (13.4 mmol) of 2-chloro-4'-fluoro-acetophenone followed by 2.0 g (24.4 mmol) of sodium bicarbonate. This mixture was heated to reflux for 1.5 hours. The reaction mixture was poured into 500 ml of brine and extracted with chloroform. The organic layer was dried with magnesium sulfate, filtered and concentrated to yield a solid which was recrystallized from 2-butanone/cyclohexane. 1-(4-Fluorophenyl)-2-[4-[(4acetamidophenyl)carbonyl]-1-piperidinyl]-ethanone was obtained as an off-white solid having amp of 168°-170° C.

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a solid which
  8. customwas recrystallized from 2-butanone/cyclohexane

Sources & evidence

ORD record
ord-c17bb95d9f644febb3070c37881dd837
Source dataset
uspto-grants-1996_03
Patent number
US05500433

Reaction notes

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