Water → HCID 86599638, compound

HRID 1174520Notes

Reaction equation

HRID 1174520 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4](OS(C)(=O)=O)[CH2:3]1.[N-:13]=[N+:14]=[N-:15].[Na+].O>CN(C=O)C>[N:13]([CH:4]1[CH2:5][CH2:6][CH2:7][N:2]([CH3:1])[CH2:3]1)=[N+:14]=[N-:15]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 55266256HCID 55266256, compound

Product 1

HCID 86599638HCID 86599638, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methanesulfonic acid 1-methyl-piperidin-3-yl ester (A) (3 g, 0.17 mmol) in DMF (35 cm3) was added sodium azide (11 g, 0.17 mol). The reaction was then heated to 80° C. for 16 h, and allowed to cool before water (80 cm3) was added and the organic material was extracted into ethyl acetate (80 cm3). The aqueous layer was then extracted with a further portion ethyl acetate (60 cm3) and the combined organic collections and washed with saturated aqueous sodium chloride solution (100 cm3). The organic mixture was and dried over sodium sulfate and then evaporated under reduced pressure to afford the title compound as a crude oil, which was used as crude in next reaction.

Workup

  1. additionwas added
  2. extractionthe organic material was extracted into ethyl acetate (80 cm3)
  3. extractionThe aqueous layer was then extracted with a further portion ethyl acetate (60 cm3)
  4. washthe combined organic collections and washed with saturated aqueous sodium chloride solution (100 cm3)
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3349a3051b4b4343aae361e73ed317b2
Source dataset
uspto-grants-2010_11
Patent number
US07838518B2

Reaction notes

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