1-Butylpiperazine → HCID 57564985, compound

HRID 1726859Notes

Reaction equation

HRID 1726859 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[NH:9][C:10]([C:15]3[CH:20]=[C:19](Cl)[CH:18]=[CH:17][N:16]=3)=[CH:11][C:12](=[O:14])[CH:13]=2)[CH:3]=1.[CH2:22]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[CH2:23][CH2:24][CH3:25]>CC(O)(CC)C>[CH2:22]([N:26]1[CH2:31][CH2:30][N:29]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]3[NH:9][C:10]([C:15]4[CH:20]=[C:19]([N:29]5[CH2:30][CH2:31][N:26]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:27][CH2:28]5)[CH:18]=[CH:17][N:16]=4)=[CH:11][C:12](=[O:14])[CH:13]=3)[CH:3]=2)[CH2:28][CH2:27]1)[CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 4243221-ButylpiperazineHCID 58781425HCID 58781425, compound

Product 1

HCID 57564985HCID 57564985, compound

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Procedure

A mixture of 1.12 g (3.52 mmol) 4,4″-dichlor-1′H-[2,2′;6′,2″]terpyridin-4′-on, 10.0 g (70 mmol) 1-butyl-piperazine and 24 mg (0.18 mmol) Zn(II)-chloride in 20 ml 2-methyl-2butanol is refluxed for 18 hours. Afterwards, the solution is concentrated by a rotary evaporator. The raw product is recrystallized from a methanol/water mixture. The yellowish 4,4″-bis-(4-butyl-piperazin-1-yl)-1′H-[2,2′;6′,2″]terpyridin-4′-on is obtained. 1H-NMR (360 MHz, CDCl3): 8.31 (d, 2H, J=5.9 Hz); 7.18 (sm, 2H); 6.94 (s, 2H); 6.65 (dd, 2H, J=5.9,1.8 Hz); 3.39-3.31 (tm, 8H); 2.55-2.47 (tm, 8H); 2.36-2,28 (tm, 4H); 1.5-1.38 (m, 4H); 1.36-1.22 (m, 4H); 0.87 (t, J=7.2 Hz, 6H).

Workup

  1. temperatureis refluxed for 18 hours
  2. concentrationAfterwards, the solution is concentrated by a rotary evaporator
  3. customThe raw product is recrystallized from a methanol/water mixture

Sources & evidence

ORD record
ord-9aa7e53f079f4a8a97f33ca8f6d99f7b
Source dataset
uspto-grants-2009_02
Patent number
US07494964B2

Reaction notes

Loading…