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Water → (E)-1-(2-chloro-alpha-methoxycarbonylbenzyl)-3-(N,N-dimethylcarbamoyl)methylidene-4-hydroxypiperidine

HRID 397610
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HRID 397610 반응식
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][N:13]([CH3:24])[C:14](/[CH:16]=[C:17]1\[CH2:18][NH:19][CH2:20][CH2:21][CH:22]\1[OH:23])=[O:15].[Cl:25][C:26]1[CH:37]=[CH:36][CH:35]=[CH:34][C:27]=1[CH:28](Br)[C:29]([O:31][CH3:32])=[O:30].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:25][C:26]1[CH:37]=[CH:36][CH:35]=[CH:34][C:27]=1[CH:28]([N:19]1[CH2:20][CH2:21][CH:22]([OH:23])/[C:17](=[CH:16]/[C:14](=[O:15])[N:13]([CH3:12])[CH3:24])/[CH2:18]1)[C:29]([O:31][CH3:32])=[O:30]
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참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10730282Methyl alpha-bromo-2-chlorophenylacetateHCID 23000841(E)-3-(N,N-dimethylcarbamoyl)methylidene-4-hydroxypiperidine p-toluenesulfonate

생성물 1

HCID 23000852(E)-1-(2-chloro-alpha-methoxycarbonylbenzyl)-3-(N,N-dimethylcarbamoyl)methylidene-4-hydroxypiperidine수율 78%

시약·촉매·용매

1
HCID 6228Dimethylformamide용매

실험 절차

7.95 g (23.3 mmol) of the (E)-3-(N,N-dimethylcarbamoyl)methylidene-4-hydroxypiperidine p-toluenesulfonate were dissolved in 50 ml of N,N-dimethylformamide (DMF), followed by the addition of 7.35 g (purity: 80.0%, 22.3 mmol) of 2-chloro-α-methoxycarbonylbenzyl bromide and 7.40 g (53.5 mmol) of potassium carbonate. The resulting mixture was stirred at room temperature for 15 hours. After completion of the reaction, 150 ml water were added. The resulting mixture was extracted with toluene and ethyl acetate. The extract was distilled under reduced pressure. The residue was then purified by chromatography on a silica gel column (eluting solvent: chloroform/methanol=9/1 to 4/1), whereby 6.38 g (77.9%) of the title compound were obtained as a yellowish brown oil.

후처리

  1. additionwere added
  2. extractionThe resulting mixture was extracted with toluene and ethyl acetate
  3. distillationThe extract was distilled under reduced pressure
  4. customThe residue was then purified by chromatography on a silica gel column (eluting solvent: chloroform/methanol=9/1 to 4/1)

출처 및 근거

ORD 기록
ord-afd36c520715487ea08bbc7da419b298
출처 데이터셋
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06610708B1

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