Piperidine → HCID 53725566, compound

HRID 1604291Notes

Reaction equation

HRID 1604291 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]1[O:9][C:8](=[O:10])[N:7]([N:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6]1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C)C=O>[C:13]1([CH:12]=[N:11][N:7]2[CH2:6][CH:5]([CH2:4][CH2:3][CH2:2][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[O:9][C:8]2=[O:10])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 53775232HCID 53775232, compound

Product 1

HCID 53725566HCID 53725566, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 5-(3-chloropropyl)-3-phenylmethyleneamino-2-oxazolidinone (2.7 g, 0.0101 mole), dimethylformamide (75 ml) and piperidine (2.15 g, 0.0253 mole, 2.5 eq.) is heated to reflux. Reflux is maintained for 2 hours. After cooling, the solution is concentrated under reduced pressure to a solid-oily residue. This residue is suspended in H2O (200 ml) then extracted with ethyl acetate (3×100 ml). The ethyl acetate is dried over MgSO4, filtered, then concentrated under reduced pressure to an oily-solid residue. This residue is triturated in hexane by stirring 1 hours. The solid is collected and air-dried giving 1.67 g (0.0053 mole) of 3-phenylmethyleneamino-5-[3-(1-piperidinyl)propyl]-2-oxazolidinone.

Workup

  1. temperatureReflux
  2. temperatureis maintained for 2 hours
  3. temperatureAfter cooling
  4. concentrationthe solution is concentrated under reduced pressure to a solid-oily residue
  5. extractionthen extracted with ethyl acetate (3×100 ml)
  6. dry with materialThe ethyl acetate is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure to an oily-solid residue
  9. customThis residue is triturated in hexane
  10. customThe solid is collected
  11. customair-dried

Sources & evidence

ORD record
ord-87eaf92f827c48d9bbc51b6a12512261
Source dataset
uspto-grants-1999_11
Patent number
US05994354

Reaction notes

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