5-Bromopentanenitrile → STK366373

HRID 723140Notes

Reaction equation

HRID 723140 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7].[C:8]1(=[O:18])[NH:12][C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12.[K]>CN(C=O)C>[O:13]=[C:11]1[C:10]2[C:9](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8](=[O:18])[N:12]1[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7]

Participants

4

Reactant 2

HCID 794355-BromopentanenitrileHCID 24194345Phthalimide potassium salt

Product 1

HCID 227606STK366373Yield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-bromovaleronitrile (5.12 g, 30.0 mmol) in DMF (40 mL) was added potassium phthalimide (6.00 g, 32.4 mmol). The above suspension was heated at 60° C. for 16 h, concentrated, and partitioned between H2O and DCM. The DCM layer was separated, washed with H2O (3×) and brine, dried over Na2SO4, and concentrated to give the title compound (6.84 g, quantitative yield) as a white solid.

Workup

  1. concentrationconcentrated
  2. custompartitioned between H2O and DCM
  3. customThe DCM layer was separated
  4. washwashed with H2O (3×) and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c68f67dbd0044715932ed41c72387d88
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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