Ammonia → 1-[Bis(4-chlorophenyl)methyl]azetidin-3-ylamine

HRID 413021

반응식

HRID 413021 반응식
[NH3:1].CS(O[CH:7]1[CH2:10][N:9]([CH:11]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:8]1)(=O)=O>CO>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH:11]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[N:9]2[CH2:10][CH:7]([NH2:1])[CH2:8]2)=[CH:13][CH:14]=1

참가 물질

4

반응물 2

HCID 222AmmoniaHCID 218966031-[Bis(4-chlorophenyl)methyl]azetidin-3-yl methylsulfonate

생성물 1

HCID 218965981-[Bis(4-chlorophenyl)methyl]azetidin-3-ylamine

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
-60 °C

실험 절차

1-[Bis(4-chlorophenyl)methyl]azetidin-3-ylamine may be obtained in the following manner: 400 cm3 of a mixture of methanol and liquid ammonia (50/50 by volume) are added to 27 g of 1-[bis(4-chlorophenyl)methyl]azetidin-3-yl methylsulfonate contained in an autoclave previously cooled to around −60° C. The reaction medium is then stirred at 60° C. for 24 hours and then abandoned in the open air to allow the evaporation of the ammonia and finally concentrated under reduced pressure (2.7 kPa). The residue is taken up in 500 cm3 of a 0.37 N aqueous sodium hydroxide solution and extracted with four times 500 cm3 of ethyl ether. The combined organic phases are washed successively with twice 100 cm3 of distilled water and 100 cm3 of a saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure (2.7 kPa). The residue obtained is purified by flash chromatography on silica gel [eluant: dichloromethane/methanol (95/5 by volume)]. 14.2 g of 1-[bis(4-chlorophenyl)methyl]azetidin-3-ylamine are obtained in the form of an oil which solidifies into a cream-colored solid.

후처리

  1. customthe evaporation of the ammonia
  2. concentrationfinally concentrated under reduced pressure (2.7 kPa)
  3. extractionextracted with four times 500 cm3 of ethyl ether
  4. washThe combined organic phases are washed successively with twice 100 cm3 of distilled water and 100 cm3 of a saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure (2.7 kPa)
  8. customThe residue obtained
  9. customis purified by flash chromatography on silica gel [eluant: dichloromethane/methanol (95/5 by volume)]

출처 및 근거

ORD 기록
ord-cd0846ac30904b529458e2e3369daa2b
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566356B2

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