1-Phenylpiperazine → HCID 86608225, compound

HRID 417871Notes

Reaction equation

HRID 417871 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]#[CH:10])(=O)=O.[C:11]1([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[CH2:6]([N:20]1[CH2:21][CH2:22][N:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:18][CH2:19]1)[CH2:7][CH2:8][C:9]#[CH:10]

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 81531DiisopropylethylamineHCID 12476209Pent-4-yn-1-yl methanesulfonate

Product 1

HCID 86608225HCID 86608225, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of pent-4-ynyl methanesulfonate (1.05 g), N-phenyl piperazine (1.02 g) and diisoproylethylamine (1.2 mL) in THF (5 mL) was heated to reflux overnight. The mixture was concentrated, diluted with aq. NaOH 2M (10 mL) and extracted with DCM (2×50 mL). Drying (Na2SO4) and silica gel flash chromatography (EtOAc/hexane 2:1→2:0) afforded 1-(pent-4-ynyl)-4-phenylpiperazine (1.03 g).

Workup

  1. temperatureto reflux overnight
  2. concentrationThe mixture was concentrated
  3. additiondiluted with aq. NaOH 2M (10 mL)
  4. extractionextracted with DCM (2×50 mL)
  5. dry with materialDrying (Na2SO4) and silica gel flash chromatography (EtOAc/hexane 2:1→2:0)

Sources & evidence

ORD record
ord-35f5e9f3fab54d3390b003830431ac85
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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