Diisopropylethylamine → 1-(Pent-4-ynyl)-4-(pyridin-2-yl)piperazine

HRID 1984098Notes

Reaction equation

HRID 1984098 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]#[CH:10])(=O)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(C(C)C)CC)(C)C>C1COCC1>[CH2:6]([N:20]1[CH2:21][CH2:22][N:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)[CH2:18][CH2:19]1)[CH2:7][CH2:8][C:9]#[CH:10]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 944591-(2-Pyridyl)piperazineHCID 12476209Pent-4-yn-1-yl methanesulfonate

Product 1

HCID 866082261-(Pent-4-ynyl)-4-(pyridin-2-yl)piperazineYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of pent-4-ynyl methanesulfonate (1.05 g), 1-(pyridin-2-yl)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-(pyridin-2-yl)piperazine (1.02 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-f5871390d0b24938bc871753e3cf0295
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

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