Tert-Butylbenzene → HCID 20311700, compound

HRID 867012Notes

Reaction equation

HRID 867012 reaction equation
[C:1]([N:4]1[CH2:12][CH2:11][CH:7]([C:8](Cl)=[O:9])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[C:1]([N:4]1[CH2:12][CH2:11][CH:7]([C:8](=[O:9])[C:20]2[CH:21]=[CH:22][C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:18][CH:19]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7366Tert-ButylbenzeneHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20311700HCID 20311700, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

19.1 g of 1-acetylisonipecotoyl chloride, Example 1(b) are added portionwise to a stirring suspension of 13 g of t-butylbenzene and 27 g of aluminum chloride in 175 ml of dichloroethane. The reaction mixture is refluxed for 1 hour, cooled, and poured onto ice. The organic layer is separated and the aqueous layer is extracted with chloroform. The organic layers are combined, dried, and the solvent is removed under reduced pressure leaving the oil 1-acetyl-4-(4-t-butylbenzoyl)piperidine.

Workup

  1. temperatureThe reaction mixture is refluxed for 1 hour
  2. temperaturecooled
  3. additionpoured onto ice
  4. customThe organic layer is separated
  5. extractionthe aqueous layer is extracted with chloroform
  6. customdried
  7. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-7e81de343e61426d9edef83ecabc576d
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Reaction notes

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