Acetone → HCID 53959004, compound

HRID 596304Notes

Reaction equation

HRID 596304 reaction equation
[Na].[OH:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([NH2:16])[CH:8]=1.[N:20]1(CCCl)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.[CH3:29][C:30](C)=O>>[NH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]1[CH2:29][CH2:30][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([NH2:16])[CH:8]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 748271-(2-Chloroethyl)piperidineHCID 5360545SodiumHCID 21451441HCID 21451441, compound

Product 1

HCID 53959004HCID 53959004, compound

Procedure

A mixture of 13.4 g of the sodium salt of 4-(3-hydroxyphenoxy)-2-amino-nitrobenzene in 100 ml of acetone was stirred with 7.5 g of piperidino-ethyl-chloride for three hours on on steam bath. Then the solvent was evaporated under reduced pressure, the residue was dissolved in diluted acetic acid and the solution was made alkaline with ammonia. To isolate the free 4-[3-(2-piperidyl-ethoxy)-phenoxy]-2-amino-nitrobenzene the emulsion was worked up over ethyl acetate and after evaporating the solvent 17 g of the compound were obtained in an oily form, which could be used directly for hydrogenation.

Workup

  1. customThen the solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in diluted acetic acid

Sources & evidence

ORD record
ord-83d52c1f08014f6c8efa73796d2c5916
Source dataset
uspto-grants-1977_03
Patent number
US04010272

Reaction notes

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