Dimethylformamide → HCID 84048021, compound

HRID 632514Notes

Reaction equation

HRID 632514 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:24]=[O:25]>C1COCC1.CCCCCC>[CH3:16][N:13]1[CH2:14][CH2:15][N:10]([CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([CH:24]=[O:25])=[CH:3][CH:4]=2)[CH2:11][CH2:12]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 11346605HCID 11346605, compoundHCID 178418339Butyllithium

Product 1

HCID 84048021HCID 84048021, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-10 °C

Procedure

To 87 mL of a solution of 8.7 g of 1-[2-(4-bromophenyl)ethyl]-4-methylpiperazine in THF cooled to −70° C. was added dropwise 21.1 mL of a solution of n-butyllithium (1.6 mol/L) in hexane, and the mixture was stirred at the same temperature for 30 minutes. While the reaction mixture was stirred at the same temperature, 3.6 mL of N,N-dimethylformamide was added dropwise. The mixture was stirred at the same temperature for 30 minutes. The cooling bath was removed, and the mixture was allowed to warm to −10° C., poured into a mixture of 12 mL of 1 N hydrochloric acid and 100 mL of cold water, and subjected to extraction with CHCl3. The obtained extract was dried over MgSO4 and concentrated to give 7.04 g of the title compound (98%).

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at the same temperature for 30 minutes
  3. customThe cooling bath was removed
  4. additionpoured into a mixture of 12 mL of 1 N hydrochloric acid and 100 mL of cold water
  5. extractionsubjected to extraction with CHCl3
  6. extractionThe obtained extract
  7. dry with materialwas dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-db0df42b9292416fa6c5e4b9f0f38f6f
Source dataset
uspto-grants-2016_04
Patent number
US09321752B2

Reaction notes

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