Cesium carbonate → HCID 59349603, compound

HRID 415098Notes

Reaction equation

HRID 415098 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].CS(O[CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 41154952-Amino-3-NitrophenolHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 59349603HCID 59349603, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A round-bottom flask was charged with 2-amino-3-nitrophenol (10.64 g, 60 mmol, commercially available from Aldrich), tert-butyl 4-(methylsulfonyloxy)-piperidine-1-carboxylate (18.05 g, 66 mmol, commercially available from AnandChem Ltd.,), DMA (100 mL) and cesium carbonate (21.6 g). The mixture was stirred at room temperature overnight. The mixture was filtered, and the recovered solid was washed with ethyl acetate. The filtrate was further diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and combined organic solvent was washed with saturated brine, dried and concentrated under reduced pressure. The residue was triturated with ether to give tert-butyl 4-(2-amino-3-nitrophenoxy)piperidine-1-carboxylate (8.0 g, 56% yield). MS (EI): 338 (MH+).

Workup

  1. filtrationThe mixture was filtered
  2. washthe recovered solid was washed with ethyl acetate
  3. additionThe filtrate was further diluted with ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwas washed with saturated brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-b9915ed86c504fdb831742128f13e674
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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