Diisopropylamine → 2-(1-Benzylpiperidin-4-yl)-1-(3-chloro-2-thienyl)ethanol

HRID 606153

反応式

HRID 606153 の反応式
C(NC(C)C)(C)C.[Cl:8][C:9]1[CH:13]=[CH:12][S:11][CH:10]=1.[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][CH:28]=[O:29])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>O1CCCC1.C([Li])CCC.C(OCC)(=O)C>[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][CH:28]([C:10]2[S:11][CH:12]=[CH:13][C:9]=2[Cl:8])[OH:29])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

8

反応物 4

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 870173-ChlorothiopheneHCID 100136024-Piperidineacetaldehyde, 1-(phenylmethyl)-

生成物 1

HCID 222481782-(1-Benzylpiperidin-4-yl)-1-(3-chloro-2-thienyl)ethanol収率 59%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 178418339Butyllithium溶媒

実験手順

After dissolving 1.3 ml of diisopropylamine in 20 ml of tetrahydrofuran, 3.5 ml of n-butyllithium (2.66 M, n-hexane solution) was added dropwise while stirring at below −30° C. After stirring for 30 minutes while cooling on ice, 0.86 ml of 3-chlorothiophene was added dropwise. The mixture was stirred for another 30 minutes, and then a solution of 1.68 g of 1-benzyl-4-piperidineacetaldehyde in tetrahydrofuran (5 ml) was added and stirring was continued for 1 hour. Saturated aqueous ammonium chloride solution was added to the reaction solution and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (1.53 g, 59% yield).

後処理

  1. additionwas added dropwise
  2. stirringAfter stirring for 30 minutes
  3. additionwas added dropwise
  4. stirringThe mixture was stirred for another 30 minutes
  5. stirringstirring
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-e4bed218e5e24e19b565bf47b8b2576c
出典データセット
uspto-grants-2011_03
特許番号
US07915274B2

関連ノート

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