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

HRID 397610
Notes
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Reaction equation

HRID 397610 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-afd36c520715487ea08bbc7da419b298
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06610708B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes