Water → HCID 18430857, compound

HRID 1278600Notes

Reaction equation

HRID 1278600 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([C:17]#[N:18])[CH3:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:28][CH2:29][CH2:30][CH2:31]CBr.O>O1CCCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2([C:17]#[N:18])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:16]2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81001,5-DibromopentaneHCID 2724682Lithium diisopropylamideHCID 18430866HCID 18430866, compound

Product 1

HCID 18430857HCID 18430857, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of l-[(4-benzyl-1-piperazinyl)methyl]ethanecarbonitrile (9.0 g/39.3 mmol) in tetrahydrofuran (300 ml) was added dropwise 2.0 M solution of lithium diisopropylamide (98 ml/197 mmol) at −78° C., and then the resulting mixture was stirred for 30 minutes. 1,5-Dibromopentane (8 ml/59 mmol) was added to the mixture in one portion and the resulting mixture was allowed to warm to ambient temperature. The mixture was stirred for 3 hours. Then, H2O (150 ml) was added for quenching. The mixture was extracted with ethyl acetate (200 ml×2). The combined extracts were washed with brine (50 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (Si, 230-400 mesh/150 g/dichloromethane:methanol=100:0-100:4) to give a brown solid (11 g/94%).

Workup

  1. stirringThe mixture was stirred for 3 hours
  2. customfor quenching
  3. extractionThe mixture was extracted with ethyl acetate (200 ml×2)
  4. washThe combined extracts were washed with brine (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (Si, 230-400 mesh/150 g/dichloromethane:methanol=100:0-100:4)
  9. customto give a brown solid (11 g/94%)

Sources & evidence

ORD record
ord-d3c3c7cffec24b62bf4b1c2c2d95cc28
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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