Ammonium Chloride → 4,5-dichloro-1-{4-[4-hydroxy-4-(4-methylphenyl)-1-piperidyl]butyl}-2-methyl-1H-imidazole

HRID 2790

반응식

HRID 2790 반응식
[Cl:1][C:2]1[N:3]=[C:4]([CH3:19])[N:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)[C:6]=1[Cl:7].[Mg+2].[Cl-].[Cl-].[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([Mg]Br)=[CH:26][CH:25]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([CH3:19])[N:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][C:15]([OH:18])([C:27]3[CH:28]=[CH:29][C:24]([CH3:23])=[CH:25][CH:26]=3)[CH2:14][CH2:13]2)[C:6]=1[Cl:7]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 5360315Magnesium ChlorideHCID 219978934,5-dichloro-2-methyl-1-(4-(4-oxo-1-piperidyl)butyl]-1H-imidazoleHCID 178418370HCID 178418370, 화합물

생성물 1

HCID 98436744,5-dichloro-1-{4-[4-hydroxy-4-(4-methylphenyl)-1-piperidyl]butyl}-2-methyl-1H-imidazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 1.0 g (3.3 mmol) of 4,5-dichloro-2-methyl-1-[4-(4-oxo-1-piperidyl)butyl]-1H-imidazole in 10 ml of anhydrous tetrahydrofuran is added to a suspension of 1.08 g (11.4 mmol) of MgCl2 in 15 ml of anhydrous THF at -40° C. and under a nitrogen atmosphere. The mixture is stirred for 5 minutes and then, at -40° C., 6.8 ml of a 1.0M solution of 4-methylphenylmagnesium bromide are added. The resulting suspension is stirred for 15 minutes at -40° C. and for 3 hours at room temperature. An aqueous ammonium chloride solution is then added and the tetrahydrofuran is evaporated. The resulting aqueous phase is extracted with chloroform. The chloroform phase is washed with water, dried with anhydrous sodium sulfate and evaporated to dryness, a crude product being obtained which is purified by chromatography on silica gel, giving 1.02 g (2.6 mmol) of 4,5-dichloro-1-{4-[4-hydroxy-4-(4-methylphenyl)-1-piperidyl]butyl}-2-methyl-1H-imidazole.

후처리

  1. stirringThe resulting suspension is stirred for 15 minutes at -40° C. and for 3 hours at room temperature
  2. customthe tetrahydrofuran is evaporated
  3. extractionThe resulting aqueous phase is extracted with chloroform
  4. washThe chloroform phase is washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customa crude product being obtained which
  8. customis purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-2c61f63832514f10a9e3abea4cbd484d
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731331

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