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Water → Ethyl 4-[[4-[1-(1-Acetoxyethyl)oxycarbonylpiperidin-4-yl]-2-oxopiperazin-1-yl]acetyl]phenoxyacetate

HRID 993041
Notes
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Reaction equation

HRID 993041 reaction equation
Cl.Cl.[O:3]=[C:4]1[CH2:9][N:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:7][CH2:6][N:5]1[CH2:16][C:17]([C:19]1[CH:31]=[CH:30][C:22]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=1)=[O:18].CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.[C:48](=O)([O:56]C1C=CC([N+]([O-])=O)=CC=1)[O:49][CH:50]([O:52][C:53](=[O:55])[CH3:54])[CH3:51].O>CN(C)C=O>[C:53]([O:52][CH:50]([O:49][C:48]([N:13]1[CH2:12][CH2:11][CH:10]([N:8]2[CH2:7][CH2:6][N:5]([CH2:16][C:17]([C:19]3[CH:31]=[CH:30][C:22]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=3)=[O:18])[C:4](=[O:3])[CH2:9]2)[CH2:15][CH2:14]1)=[O:56])[CH3:51])(=[O:55])[CH3:54]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 88675Proton spongeHCID 117805601-acetoxyethyl p-nitrophenyl carbonateHCID 18408903HCID 18408903, compound

Product 1

HCID 18408908Ethyl 4-[[4-[1-(1-Acetoxyethyl)oxycarbonylpiperidin-4-yl]-2-oxopiperazin-1-yl]acetyl]phenoxyacetateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 107 mg of ethyl 4-[[2-oxo-4-(piperidin-4-yl)piperazin-1-yl]acetyl]phenoxyacetate dihydrochloride synthesized according to the method described in WO962503 in 2 ml of N,N-dimethylformamide were added 110 mg of proton sponge and 85.7 mg of 1-acetoxyethyl 4-nitrophenyl carbonate with stirring at 0° C., and the mixture was stirred at room temperature for 18 hours. The reaction mixture was poured into 2 ml of water and extracted three times with 4 ml of ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The residue thus obtained was purified by chromatography on an LH-20 column (chloroform:methanol=1:1) to give 119 mg of the title compound (100%).

Workup

  1. customsynthesized
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. extractionextracted three times with 4 ml of ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was removed by distillation
  6. customThe residue thus obtained
  7. customwas purified by chromatography on an LH-20 column (chloroform:methanol=1:1)

Sources & evidence

ORD record
ord-c4b5436f4a4144fbb1d2cb1f99bef700
Source dataset
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06472397B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes