Diisopropylamine → Ammonia

HRID 355430노트

반응식

HRID 355430 반응식
C([Li])CCC.C([NH:9]C(C)C)(C)C.C([N-]C(C)C)(C)C.[Li+].[C:21]([C:24]1[CH:37]=[CH:36][C:35]2[S:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][C:26]=2[CH:25]=1)(=[O:23])[CH3:22].[N:38]12[CH2:45][CH2:44][CH:41]([CH2:42][CH2:43]1)[C:40](=[O:46])[CH2:39]2>C(Cl)(Cl)Cl.CO.O.C1COCC1.CCCCCC>[NH3:9].[CH:25]1[C:26]2[NH:27][C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[S:34][C:35]=2[CH:36]=[CH:37][C:24]=1[C:21]([CH2:22][C:40]1([OH:46])[CH:41]2[CH2:44][CH2:45][N:38]([CH2:43][CH2:42]2)[CH2:39]1)=[O:23]

참가 물질

12

반응물 5

HCID 7912DiisopropylamineHCID 195073-QuinuclidinoneHCID 81131Methyl phenothiazin-2-yl ketoneHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

생성물 2

HCID 222Ammonia수율 29%HCID 18942260HCID 18942260, 화합물수율 7%

시약·촉매·용매 5

HCID 887Methanol용매HCID 962Water용매HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

실험 절차

In an atmosphere of argon, a hexane solution of n-butyl lithium (1.71M, 6.1 ml, 10.5 mmol) was added at -78° C. to a THF (10 ml) solution of diisopropylamine (1.54 ml, 11 mmol), and the mixture was stirred for 40 minutes. To the resulting solution of lithium diisopropylamide was added a THF (8 ml) solution of 2-acetylphenothiazine (1.21 g, 5.0 mmol). The mixture was stirred for 30 minutes, a THF (3 ml) solution of 3-quinuclidinone (626 mg, 5.0 mmol) was added, and the mixture was stirred for 30 minutes. Water was added to the reaction mixture and the reaction product was extracted with chloroform. The extract was washed with saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; 29% aqueous ammonia:methanol:chloroform=0.8:8:92 then 2:20:80), to give the title compound (127 mg, 0.35 mmol, 7%) as yellow foam.

후처리

  1. stirringThe mixture was stirred for 30 minutes
  2. stirringthe mixture was stirred for 30 minutes
  3. extractionthe reaction product was extracted with chloroform
  4. washThe extract was washed with saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent

출처 및 근거

ORD 기록
ord-5d45b6d7cd664394bae14a95d81d6963
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05830902

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