1-Phenylpiperazine → 1-(But-3-yn-1-yl)-4-phenylpiperazine

HRID 417868Notes

Reaction equation

HRID 417868 reaction equation
C[C:2]1[CH:7]=[CH:6][C:5](S(OCCC#C)(=O)=O)=[CH:4][CH:3]=1.[C:16]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)C=C[CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C>ClCCCl>[CH2:16]([N:22]1[CH2:27][CH2:26][N:25]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:24][CH2:23]1)[CH2:17][C:18]#[CH:19]

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 81531DiisopropylethylamineHCID 2720203-Butynyl p-toluenesulfonate

Product 1

HCID 189930381-(But-3-yn-1-yl)-4-phenylpiperazine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of but-3-ynyl 4-methylbenzenesulfonate (1.72 g), N-phenyl piperazine (1.17 mL) and diisoproylethylamine (1.45 mL) in 1,2-dichloroethane (5 mL) was heated to reflux overnight. The mixture was concentrated, diluted with sat. aq. NaHCO3 (5 mL) and extracted with DCM (2×50 mL). Drying (Na2SO4) and silica gel flash chromatography (3% Et3N in EtOAc) afforded 1-(but-3-ynyl)-4-phenylpiperazine (0.76 g)

Workup

  1. temperatureto reflux overnight
  2. concentrationThe mixture was concentrated
  3. additiondiluted with sat. aq. NaHCO3 (5 mL)
  4. extractionextracted with DCM (2×50 mL)
  5. dry with materialDrying (Na2SO4) and silica gel flash chromatography (3% Et3N in EtOAc)

Sources & evidence

ORD record
ord-fb33b3f0edf14a1aaaf7388bb7fd46db
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

Loading…