Benzyl Bromide → HCID 19390903, compound

HRID 1645864Notes

Reaction equation

HRID 1645864 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][CH2:18][CH3:19])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)C>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:18][CH3:19])=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 19390924HCID 19390924, compound

Product 1

HCID 19390903HCID 19390903, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 30 ml of ethanol was dissolved 3.13 g of the 1-acetyl-4-[4-(ethylamino)benzyl]piperidine (Compound No. 8) prepared in Example 16, followed by addition of 3.31 g of potassium carbonate and 1.43 ml of benzyl bromide. The mixture was refluxed for 2 hours and the insolubles were filtered off. The solvent was then distilled off and the remaining oil was purified by silica gel column chromatography (eluent: ethyl acetate) to give 3.8 g of the title compound as a colorless oil.

Workup

  1. custom8) prepared in Example 16
  2. temperatureThe mixture was refluxed for 2 hours
  3. filtrationthe insolubles were filtered off
  4. distillationThe solvent was then distilled off
  5. customthe remaining oil was purified by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-7d3fbcb487d14e87bd7c413acbe5d674
Source dataset
uspto-grants-1993_01
Patent number
US05177087

Reaction notes

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