반응 #60493

ord-dfe99c3ce2a543f192d80bfdd4dfe622

반응 조건

온도
220°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타During the reaction
  2. 2
    기타the excess hydrogen chloride gas in the reactor was removed several times with nitrogen gas
  3. 3
    workup.STIRRINGthe mixture was stirred for 1 hour under the same conditions
  4. 4
    온도The reaction mixture was cooled to room temperature
  5. 5
    추출extraction
  6. 6
    추출The aqueous layer was again extracted with chloroform
  7. 7
    세척washed with brine
  8. 8
    건조dried over anhydrous magnesium sulfate
  9. 9
    여과The desiccant was filtered off
  10. 10
    농축the filtrate was concentrated under reduced pressure
  11. 11
    기타The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

실험 절차

A mixture of the crude product of 4-methoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenylamine produced in Example (85b), bis(2-chloroethyl)amine hydrochloride (770 mg, 4.33 mmol) and 1,2-dichlorobenzene (10 ml) was stirred for 2 hours at an external temperature of 220° C. During the reaction, the excess hydrogen chloride gas in the reactor was removed several times with nitrogen gas. Bis(2-chloroethyl)amine hydrochloride (180 mg, 1.01 mmol) was then added and the mixture was stirred for 1 hour under the same conditions. The reaction mixture was cooled to room temperature, saturated aqueous solution of sodium hydrogencarbonate was added and extraction was performed with chloroform. The aqueous layer was again extracted with chloroform, and the organic layers were combined, washed with brine and then dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 660 mg of the title compound as a brown solid.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07425554B2uspto-grants-2008_09