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

HRID 397610
ノート
印刷プレビュー

反応式

HRID 397610 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒

1
HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-afd36c520715487ea08bbc7da419b298
出典データセット
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06610708B1

反応ノート

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