Bromine → HCID 178515393, compound

HRID 1713145Notes

Reaction equation

HRID 1713145 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([O:17]CC)=O)[C:10](=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:22][NH2:23].BrBr.C([O-])(O)=O.[Na+]>CCO.C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2[CH:14]=[C:15]([OH:17])[N:23]=[N:22][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 24408BromineHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 57420583HCID 57420583, compound

Product 1

HCID 178515393HCID 178515393, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl (1-benzyl-3-oxopiperidin-4-yl)acetate (11.4 g, 41.4 mmol) and hydrazine monohydrate (3.1 g, 62 mmol) in EtOH (50 mL) is stirred at 80° C. for one hour. The resulting solution is cooled, and concentrated in vacuo to give a white solid. The white solid is dissolved in acetic acid (120 mL) and the mixture is heated at 85° C. To the reaction mixture is added bromine (6.62 g, 41.4 mmol) dropwise. The resulting mixture is heated for another 30 min. The solvent is removed in vacuo to give a residue. A saturated NaHCO3 solution is added until pH ˜8 while stirring. The formed solid is filtered and dried in air to afford the title compound.

Workup

  1. temperatureThe resulting solution is cooled
  2. concentrationconcentrated in vacuo
  3. customto give a white solid
  4. temperaturethe mixture is heated at 85° C
  5. temperatureThe resulting mixture is heated for another 30 min
  6. customThe solvent is removed in vacuo
  7. customto give a residue
  8. stirringwhile stirring
  9. filtrationThe formed solid is filtered
  10. customdried in air

Sources & evidence

ORD record
ord-b7cf8d1d17ed4c179b571ba812af0086
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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