Cesium carbonate → HCID 67974225, compound

HRID 2174469Notes

Reaction equation

HRID 2174469 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Cl[CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][CH2:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 691274-Chloro-3-nitrophenolHCID 104870044-(2-chloroethyl)piperidine

Product 1

HCID 67974225HCID 67974225, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-chloro-3-nitrophenol (2.5 g, 14.4 mmol, 1 eq.) was placed in dimethylformamide (48 mL) with 4-(2-chloro-ethyl)piperidine (8 g, 43.2 mmol, 3 eq.), Cs2CO3 (33 g, 100.8 mmol, 7 eq.), KI (5.3 g, 31.7 mmol, 2.2 eq.). The reaction mixture was heated at 80° C. and stirred for 20 hours. The reaction mixture was then concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate. The organic phase was washed with a 1% NaOH aqueous solution, dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford 4-(2-(4-chloro-3-nitrophenoxy)ethyl)piperidine (2.3 g, 56%).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionthe resulting residue was diluted with ethyl acetate
  3. washThe organic phase was washed with a 1% NaOH aqueous solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f293ecc095c44665ad213e3c7bd45480
Source dataset
uspto-grants-2015_06
Patent number
US09061999B2

Reaction notes

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