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

HRID 890019

반응식

HRID 890019 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매HCID 178418339Butyllithium용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-637e119ec0454fe9b5e785f83e462072
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995144B2

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