Diisopropylamine → Ammonia

HRID 355430ノート

反応式

HRID 355430 の反応式
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]

参加物

12

反応物 5

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

生成物 2

HCID 222Ammonia収率 29%HCID 18942260HCID 18942260、化合物収率 7%

試薬・触媒・溶媒 5

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5d45b6d7cd664394bae14a95d81d6963
出典データセット
uspto-grants-1998_11
特許番号
US05830902

反応ノート

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