Potassium Iodide → 1-[(Benzo-1,4-dioxan-2-yl)-methyl]-4-(5-chloro-2-nitroanilino)-piperidine

HRID 2417802Notes

Reaction equation

HRID 2417802 reaction equation
Br[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.Br.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([N+:28]([O-:30])=[O:29])=[C:19]([CH:27]=1)[NH:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(C(C)=O)(C)C.O>[O:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4][CH:3]1[CH2:2][N:24]1[CH2:25][CH2:26][CH:21]([NH:20][C:19]2[CH:27]=[C:15]([Cl:14])[CH:16]=[CH:17][C:18]=2[N+:28]([O-:30])=[O:29])[CH2:22][CH2:23]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 983332-Bromomethyl-1,4-benzodioxaneHCID 204466934-(5-Chloro-2-nitroanilino)-piperidine hydrobromide

Product 1

HCID 204467111-[(Benzo-1,4-dioxan-2-yl)-methyl]-4-(5-chloro-2-nitroanilino)-piperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 112513-Methyl-2-butanoneSolvent

Procedure

11.5 g of 2-bromomethyl-1,4-benzodioxane, 20.4 g of 4-(5-chloro-2-nitroanilino)-piperidine hydrobromide, 20 g of potassium carbonate and 0.5 g of potassium iodide were dissolved in 120 ml of methyl isopropyl ketone and the solution was heated under reflux for 24 hours. After the mixture had been cooled, water was added and the organic phase was separated off, dried and concentrated.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 24 hours
  3. temperatureAfter the mixture had been cooled
  4. customthe organic phase was separated off
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-241920d0884c49228990511222590c2c
Source dataset
uspto-grants-1984_09
Patent number
US04470989

Reaction notes

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