Bromobenzene → HCID 13363395, compound

HRID 867003Notes

Reaction equation

HRID 867003 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].[Cl-].[Al+3].[Cl-].[Cl-].[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)CCl>[C:1]([N:4]1[CH2:12][CH2:11][CH:7]([C:8](=[O:9])[C:21]2[CH:22]=[CH:23][C:18]([Br:17])=[CH:19][CH:20]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13363395HCID 13363395, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

32.0 g of 1-acetylisonipecotoyl chloride, Example 1(b) are added portionwise to a stirred mixture of 45.3 g of aluminum chloride, 28.3 g of bromobenzene and 120 ml of ethylene dichloride. The solution is stirred overnight, poured onto ice, the organic phase is collected, and the aqueous layer is extracted with chloroform. The organic solutions are combined, dried, and the solvent is removed under reduced pressure to give a yellow oil which crystallizes to a soft solid. The solid is triturated with ether, collected and dried to give 1-acetyl-4-(4-bromobenzoyl)piperidine.

Workup

  1. additionpoured onto ice
  2. customthe organic phase is collected
  3. extractionthe aqueous layer is extracted with chloroform
  4. customdried
  5. customthe solvent is removed under reduced pressure
  6. customto give a yellow oil which
  7. customcrystallizes to a soft solid
  8. customThe solid is triturated with ether
  9. customcollected
  10. customdried

Sources & evidence

ORD record
ord-409255d15f8b408fa08b756a4133c85f
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Reaction notes

Loading…