Diisopropylethylamine → 1-(But-3-yn-1-yl)-4-(pyridin-2-yl)piperazine

HRID 417869Notes

Reaction equation

HRID 417869 reaction equation
[CH3:1][C:2]1C=CC(S(OCCC#C)(=O)=O)=[CH:4][CH:3]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(N(C(C)C)CC)(C)C>ClCCCl>[CH2:4]([N:25]1[CH2:24][CH2:23][N:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=2)[CH2:27][CH2:26]1)[CH2:3][C:2]#[CH:1]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 944591-(2-Pyridyl)piperazineHCID 2720203-Butynyl p-toluenesulfonate

Product 1

HCID 197352541-(But-3-yn-1-yl)-4-(pyridin-2-yl)piperazineYield 48.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of but-3-ynyl 4-methylbenzenesulfonate (1.27 g), 1-(pyridin-2-yl)piperazine (1.17 g) and diisoproylethylamine (1.37 mL) in 1,2-dichloroethane (7 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 (EtOAc/hexane 1:1→1:0) afforded 1-(but-3-ynyl)-4-(pyridin-2-yl)piperazine (0.59 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 (EtOAc/hexane 1:1→1:0)

Sources & evidence

ORD record
ord-369eccddfa7546029531f5cd485b6c7d
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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