Réaction #725894

ord-aaaf3cd83c2b4643bc5b4bb389e8ae5a

Équation de réaction

COC(=O)CCCCCOc1ccc(NC(C)=O)cc1
6-(4-Acetylaminophenoxy)hexanoic acid methyl ester
COC(=O)CCCCCOc1ccc(NC(C)=O)cc1
6-(4-Acetylamino-phenoxy)-hexanoic acid methyl ester
Cl
hydrochloric acid
Cl.Nc1ccc(OCCCCCC(=O)O)cc1
20
Rendement 55.6%
Cl.Nc1ccc(OCCCCCC(=O)O)cc1
6-(4-Amino-phenoxy)-hexanoic acid Hydrochloride
Rendement 55.6%

Conditions de réaction

Température
10°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurewas refluxed for 48 hours
  2. 2
    workup.DISTILLATIONExcess concentrated hydrochloric acid was distilled off in vacuum
  3. 3
    Filtrationfiltered hot
  4. 4
    Filtrationfiltered
  5. 5
    Autredried

Mode opératoire

A mixture of 6-(4-Acetylaminophenoxy)hexanoic acid methyl ester 19 (290 grams, 1.04 mol) in concentrated hydrochloric acid (7.12 L) was refluxed for 48 hours. Excess concentrated hydrochloric acid was distilled off in vacuum and filtered hot. The mixture was cooled to 10° C., filtered and dried give pure 20 (150 g, 55.6%) as a brown powder. The melting point was found to be 155-160° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07691364B2uspto-grants-2010_04