Piperidine → HCID 68432142, compound

HRID 1867451Notes

Reaction equation

HRID 1867451 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH:4]([N:9]1[C:15](=[O:16])[CH2:14][CH2:13][N:12]([C:17](=[O:28])/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[CH2:11][CH2:10]1)[CH2:5][CH2:6][CH2:7]I.[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O>[CH3:1][O:2][C:3](=[O:29])[CH:4]([N:9]1[C:15](=[O:16])[CH2:14][CH2:13][N:12]([C:17](=[O:28])/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[CH2:11][CH2:10]1)[CH2:5][CH2:6][CH2:7][N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10796Cesium carbonateHCID 68434105HCID 68434105, compound

Product 1

HCID 68432142HCID 68432142, compoundYield 842.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.111 g (0.20 mmol) of 2-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-5-iodo-pentanoic acid methyl ester in 1 ml of DMA was treated at 0° C. with 0.021 ml (0.21 mmol) of piperidine and stirred 30 min at 0° C. and 1 h at RT. 0.065 g (0.20 mmol) of cesium carbonate was added at 0° C. and stirring was continued for 2 h. After additional 3 h at RT, the reaction was extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl, dried over Na2SO4 evaporated and precipitated with CH2Cl2/n-pentane to yield 0.86 g (84%) of the title compound as a white foam. MS: 510.3 (MH+, 2Cl).

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. waitAfter additional 3 h at RT
  4. extractionthe reaction was extracted with aqueous saturated NaHCO3/Et2O (3×)
  5. washThe organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customprecipitated with CH2Cl2/n-pentane

Sources & evidence

ORD record
ord-e4162a8272b64f60bde8fbc2f45b0258
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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