Tetrahydrofuran → HCID 20065177, compound

HRID 359548Notes

Reaction equation

HRID 359548 reaction equation
[OH:1][C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:10](=[O:12])[CH3:11])[CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.O1CCCC1.C1CNC(=O)C1.[Br:30][Br-]Br>CCOCC>[Br:30][CH2:11][C:10](=[O:12])[C:2]([OH:1])([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:3][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 20065178HCID 20065178, compound

Product 1

HCID 20065177HCID 20065177, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Hydroxy-2-phenyl-1-piperidino-3-butanone (2.47 g, 10 mmole) is added to 50 mL of dry tetrahydrofuran (THF). The solution is stirred and a solution of pyrrolidone hydrotribromide (5 g, 10 mmole) in 100 mL of dry. THF is added dropwise over a period of 2 hours. After being refluxed for 4 hours, the reaction mixture is allowed to cool. Ether is added and the solution washed twice with water and dried over magnesium sulfate. The solvent is removed under reduced pressure and the product purified by flash column chromatography to give 4-bromo-2-hydroxy-2-phenyl 1-piperidino-3-butanone.

Workup

  1. temperatureAfter being refluxed for 4 hours
  2. temperatureto cool
  3. washthe solution washed twice with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe product purified by flash column chromatography

Sources & evidence

ORD record
ord-9688913dbeb54b0f9018f85be57b5983
Source dataset
uspto-grants-1991_03
Patent number
US05001160

Reaction notes

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