Benzyl Bromide → HCID 70373452, compound

HRID 1709872Notes

Reaction equation

HRID 1709872 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH:5]1[CH2:10][CH2:9][CH2:8][NH:7][CH2:6]1)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH2:18]([Br:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[BrH:25].[CH2:1]([O:3][C:4]([CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6]1)=[O:11])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 98969Ethyl nipecotate

Product 1

HCID 70373452HCID 70373452, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 35.4 g (0.225 mole) of (±) ethylnipecotate and 31.8 g (0.3 mole) of anhydrous sodium carbonate in 300 ml of absolute ethanol was added dropwise 41 g (0.24 mole) of benzylbromide and the mixture was stirred at ambient temperature for 24 hr. The mixture was filtered and the filtrate was concentrated. The residue was partitioned between 250 ml of methylene chloride and 250 ml of a 5% sodium hydroxide solution. The organic layer was washed with brine, dried over sodium sulfate, and concentrated to give a gummy residue. The residue was triturated with ethyl ether, filtered, and the filtrate treated with hydrogen bromide gas. The solid which precipitated was collected by filtration and recrystallized from 2-propanol to yield 35.0 g (47%) of the title compound as a white solid, mp 148°-152° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was partitioned between 250 ml of methylene chloride and 250 ml of a 5% sodium hydroxide solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a gummy residue
  8. customThe residue was triturated with ethyl ether
  9. filtrationfiltered
  10. additionthe filtrate treated with hydrogen bromide gas
  11. customThe solid which precipitated
  12. filtrationwas collected by filtration
  13. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-c8a67ead56094172a4a55209fdb17ecd
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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