Ammonia → 4-(4-Oxocyclohexyl)benzamide

HRID 1961456Notes

Reaction equation

HRID 1961456 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([CH:11]2[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:18](Cl)(=[O:22])C(Cl)=O.[NH3:24]>C(Cl)Cl.O>[O:17]=[C:14]1[CH2:15][CH2:16][CH:11]([C:5]2[CH:10]=[CH:9][C:8]([C:18]([NH2:24])=[O:22])=[CH:7][CH:6]=2)[CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 786054-PhenylcyclohexanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 153851494-(4-Oxocyclohexyl)benzamideYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

14.24 g (107 mmol) AlCl3 was added portionwise to a solution of 6.98 g (40 mmol) 4-phenylcyclohexanone and 4.51 ml (53.3 mmol) oxalylchloride in 200 ml CH2Cl2 at 0° C. Stirred at 0° C. for 1 h and at r.t. for 2 h. Cooled to 0° C. and aqueous NH3 was added carefully until pH>10. The mixture was diluted with CH2Cl2 and water. The mixture was filtered to remove solids. The phases were separated. The organic phase was dried (MgSO4) and concentrated. Gave 4.8 g (55%) of the title compound. Used in the next step without further purification.

Workup

  1. temperatureCooled to 0° C.
  2. filtrationThe mixture was filtered
  3. customto remove solids
  4. customThe phases were separated
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7f7cc252feb94fbabc80da48f8e7adc3
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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