Sodium Hydroxide → 1-(4-Bromophenyl)pyrrolidine

HRID 2361558Notes

Reaction equation

HRID 2361558 reaction equation
[C:1]1([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:12]N1C(=O)CCC1=O.[OH-].[Na+]>O1CCCC1>[Br:12][C:4]1[CH:5]=[CH:6][C:1]([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 777261-Phenylpyrrolidine

Product 1

HCID 70164571-(4-Bromophenyl)pyrrolidineYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-phenylpyrrolidine (73.8 g, 0.501 moL) in tetrahydrofuran (500 mL) was added N-bromosuccinimide (124.8 g, 1.4 equivalents) at 20° C. to 30° C., and the mixture was stirred at the same temperature for 4 hr. 1 mol/L Aqueous sodium hydroxide solution (300 mL) was added to the mixture at 27° C., and the mixture was partitioned. The organic layer was dried over anhydrous magnesium sulfate and filtered naturally, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from methanol to give the title compound (97.4 g, brown crystals). yield 86%. melting point 88.1° C.

Workup

  1. customthe mixture was partitioned
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered naturally
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-ca16bef3f2354494a6f40068e7c94df4
Source dataset
uspto-grants-2014_04
Patent number
US08691718B2

Reaction notes

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