Potassium Iodide → HCID 59641956, compound

HRID 2250477Notes

Reaction equation

HRID 2250477 reaction equation
[C:1]([N:8]([CH:10]1[CH2:14][CH2:13][NH:12][CH2:11]1)[CH3:9])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CN(C=O)C>[C:4]([O:3][C:1](=[O:2])[N:8]([CH:10]1[CH2:14][CH2:13][N:12]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:11]1)[CH3:9])([CH3:6])([CH3:7])[CH3:5]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 27614043-(N-tert-Butoxycarbonyl-N-methylamino)pyrrolidine

Product 1

HCID 59641956HCID 59641956, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(N-BOC-N-methylamino)pyrrolidine (150 mg, 0.75 mmol) in DMF (1.5 mL) was added potassium iodide (25 mg, 0.15 mmol) and potassium carbonate (207 mg, 1.50 mmol) followed by 1-bromopentane (0.097 mL, 0.78 mmol). The mixture was stirred 7 h at room temperature. Most of the DMF was then removed under low pressure and the residue partitioned between dichloromethane and water. The organic layer was dried over sodium sulfate and concentrated to give the title compound (198 mg, 98% yield) as an oil. MS m/e 271.

Workup

  1. customMost of the DMF was then removed under low pressure
  2. customthe residue partitioned between dichloromethane and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0ac18ad809c04b27b1eb8da8c37d0406
Source dataset
uspto-grants-2008_01
Patent number
US07317032B2

Reaction notes

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