Dimethylformamide → HCID 85888956, compound

HRID 1989825Notes

Reaction equation

HRID 1989825 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:3][CH:2]=1.[Li]CCCC.CN([CH:29]=[O:30])C.[OH-].[Na+]>C(OCC)C>[CH3:14][N:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:4]2[CH:3]=[CH:2][C:1]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:6][C:5]=2[CH:29]=[O:30])[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 2838321HCID 2838321, compoundHCID 178418339Butyllithium

Product 1

HCID 85888956HCID 85888956, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-biphenyl-4-ylmethyl-4-methyl-piperazine (26 mmol) in diethyl ether (50 mL) was added n-BuLi (38 mmol) and DMF (15 mL) and was refluxed for 6 h. The reaction was cooled and added 2 N NaOH (50 mL) and extracted with diethyl ether. Evaporation in vacuo gave a black oil that was purified by flash chromatography. Yield: 28% as black oil.

Workup

  1. temperaturewas refluxed for 6 h
  2. temperatureThe reaction was cooled
  3. extractionextracted with diethyl ether
  4. customEvaporation in vacuo
  5. customgave a black oil that
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-000ed9ecc40e4bb687ad523642949511
Source dataset
uspto-grants-2010_01
Patent number
US07642367B2

Reaction notes

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