Acetyl bromide → 1-benzyl-4-[N-(2-nitrophenyl)-N-acetylamino]-piperidine hydrobromide

HRID 647822Notes

Reaction equation

HRID 647822 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:25]([Br:28])(=[O:27])[CH3:26]>O1CCOCC1>[BrH:28].[CH2:2]([N:9]1[CH2:14][CH2:13][CH:12]([N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])[C:25](=[O:27])[CH3:26])[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 10482Acetyl bromideHCID 204833521-Benzyl-4-(2-nitroanilino)-piperidine hydrochloride

Product 1

HCID 204833491-benzyl-4-[N-(2-nitrophenyl)-N-acetylamino]-piperidine hydrobromide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In this reference example, 1.67 g of 1-benzyl-4-(2-nitroanilino)-piperidine hydrochloride is suspended in 30 ml of dioxane. The suspension is mixed with 13 ml of acetyl bromide and refluxed for 4 hours. The resultant reaction mixture is cooled and then the deposited crystals are separated by filtration. The crystals are washed with ether and then dried to obtain 1.96 g of crude crystals. The crude crystals are recrystallized from 25 ml of ethanol to obtain 1.33 g of the desired product.

Workup

  1. temperaturerefluxed for 4 hours
  2. customThe resultant reaction mixture
  3. temperatureis cooled
  4. customthe deposited crystals are separated by filtration
  5. washThe crystals are washed with ether
  6. customdried
  7. customto obtain 1.96 g of crude crystals
  8. customThe crude crystals are recrystallized from 25 ml of ethanol

Sources & evidence

ORD record
ord-27bf3cb579b446ac99d1112e9cdd27c4
Source dataset
uspto-grants-1983_10
Patent number
US04410528

Reaction notes

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