Hydrochloric Acid → HCID 13363395, compound

HRID 1980129Notes

Reaction equation

HRID 1980129 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:12]([N:15]1[CH2:20][CH2:19][CH:18]([C:21](Cl)=[O:22])[CH2:17][CH2:16]1)(=[O:14])[CH3:13].Cl>>[C:12]([N:15]1[CH2:16][CH2:17][CH:18]([C:21](=[O:22])[C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:19][CH2:20]1)(=[O:14])[CH3:13]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13363395HCID 13363395, compoundYield 34%

Procedure

To a stirred and warm (40° C.) mixture of 600 parts of bromobenzene and 223 parts of aluminum chloride were added portionwise 168.8 parts of 1-acetyl-4-piperidinecarbonyl chloride. Upon completion, stirring was continued for 1 hour at 50° C. and overnight at room temperature. The reaction mixture was poured onto a mixture of 1500 parts of crushed ice and hydrogen chloride. The whole was stirred thoroughly. The precipitated product was filtered off, washed with 2,2'-oxybispropane and dissolved in a mixture of 2250 parts of trichloromethane and 200 parts of water. The layers were separated. The organic layer was dried, filtered and evaporated. The solid residue was suspended in 280 parts of 2,2'-oxybispropane. The product was filtered off and dried, yielding 94 parts (34%) of 1-acetyl-4-(4-bromobenzoyl)piperidine; mp. 120° C. (intermediate 15).

Workup

  1. temperaturewarm
  2. stirringUpon completion, stirring
  3. stirringThe whole was stirred thoroughly
  4. filtrationThe precipitated product was filtered off
  5. washwashed with 2,2'-oxybispropane
  6. dissolutiondissolved in a mixture of 2250 parts of trichloromethane and 200 parts of water
  7. customThe layers were separated
  8. customThe organic layer was dried
  9. filtrationfiltered
  10. customevaporated
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-3533952857434d0c9303fb08ad6fab08
Source dataset
uspto-grants-1984_11
Patent number
US04485107

Reaction notes

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