Dimethylformamide → 2-(4-Bromophenyl)-1-methylpyrrolidine

HRID 468775Notes

Reaction equation

HRID 468775 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.[C:13](=O)([O-])[O-].[K+].[K+].CN(C)C=O.CI>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[CH3:13])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 42814942-(4-Bromophenyl)pyrrolidine

Product 1

HCID 2848972-(4-Bromophenyl)-1-methylpyrrolidineYield 44.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(4-bromophenyl)pyrrolidine (231.9 mg, 1.026 mmol) and potassium carbonate (216.6 mg, 1.567 mmol) was added N,N-dimethylformamide (4.0 mL, 52 mmol) and methyl iodide (77 uL, 1.2 mmol). The reaction mixture was stirred at room temperature for 2 days and then methyl iodide (39.0 uL, 0.626 mmol) was added. After stirring at room temperature for an additional two hours, the reaction mixture was poured into ethyl acetate and washed three times with 2M aqueous Na2CO3. The ethyl acetate layer was then dried over MgSO4, filtered, and evaporated in vacuo to yield 108.9 mg (44%) of 2-(4-bromophenyl)-1-methylpyrrolidine. LCMS (ESI): M+H=240.2.

Workup

  1. stirringAfter stirring at room temperature for an additional two hours
  2. washwashed three times with 2M aqueous Na2CO3
  3. dry with materialThe ethyl acetate layer was then dried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-05c1b26336814a56bb93b2fd05f30a60
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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